TY  - CONF
AU  - Živković, Marijana
AU  - Novaković, Irena
AU  - Matić, Ivana
AU  - Sladić, Dušan
AU  - Krstić, Natalija
PY  - 2022
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/5783
AB  - Usled stalne potrebe za novim antitumorskim lekovima, počevši od androstanskog  bis(semikarbazona), sintetisan je novi bis(karbazatni) estar (bisKBZ) za koji je određena  antimikrobna aktivnost, citotoksična aktivnost na tri maligne ćelijske linije, i urađen je  brine shrimp test toksičnosti. Novo jedinjenje se nije pokazalo kao dobar antimikrobni  agens, ispoljilo je umerenu citotoksičnost prema testiranim ćelijskim linijama i pokazalo se  kao pet puta manje toksično od cisplatina za račiće Artemia salina što je u dobroj korelaciji  sa citotoksičnošću prema HeLa ćelijskoj liniji.
AB  - Due to the constant need for new antitumor drugs, starting from androstane  bis(semicarbazone), a new bis(carbazate) ester (bis-KBZ) was synthesized; antimicrobial  activity and cytotoxicity against three malignant cell lines were determined, and the brine  shrimp toxicity test was performed. The new compound did not prove to be a good  antimicrobial agent, it showed moderate cytotoxicity to the tested cell lines, and proved to  be five times less toxic than cisplatin to Artemia salina, which correlates well with the  cytotoxicity to HeLa cell line.
PB  - Belgrade: Serbian Chemical Society
C3  - Book of Abstracts, Proceedings - 58th Meeting of the Serbian Chemical Society, Belgrade, Serbia, June 9-10, 2022 / Kratki izvodi radova, kjniga radova - 58. Savetovanje Srpskog hemijskog društva, Beograd 9. i 10. jun 2022. godine
T1  - Citotoksičnost novog steroidnog bis(karbazatnog) estra
T1  - Cytotoxicity of a new steroidal bis(carbazate) ester
SP  - 93
EP  - 93
UR  - https://hdl.handle.net/21.15107/rcub_cer_5783
ER  - 

@conference{
author = "Živković, Marijana and Novaković, Irena and Matić, Ivana and Sladić, Dušan and Krstić, Natalija",
year = "2022",
abstract = "Usled stalne potrebe za novim antitumorskim lekovima, počevši od androstanskog  bis(semikarbazona), sintetisan je novi bis(karbazatni) estar (bisKBZ) za koji je određena  antimikrobna aktivnost, citotoksična aktivnost na tri maligne ćelijske linije, i urađen je  brine shrimp test toksičnosti. Novo jedinjenje se nije pokazalo kao dobar antimikrobni  agens, ispoljilo je umerenu citotoksičnost prema testiranim ćelijskim linijama i pokazalo se  kao pet puta manje toksično od cisplatina za račiće Artemia salina što je u dobroj korelaciji  sa citotoksičnošću prema HeLa ćelijskoj liniji., Due to the constant need for new antitumor drugs, starting from androstane  bis(semicarbazone), a new bis(carbazate) ester (bis-KBZ) was synthesized; antimicrobial  activity and cytotoxicity against three malignant cell lines were determined, and the brine  shrimp toxicity test was performed. The new compound did not prove to be a good  antimicrobial agent, it showed moderate cytotoxicity to the tested cell lines, and proved to  be five times less toxic than cisplatin to Artemia salina, which correlates well with the  cytotoxicity to HeLa cell line.",
publisher = "Belgrade: Serbian Chemical Society",
journal = "Book of Abstracts, Proceedings - 58th Meeting of the Serbian Chemical Society, Belgrade, Serbia, June 9-10, 2022 / Kratki izvodi radova, kjniga radova - 58. Savetovanje Srpskog hemijskog društva, Beograd 9. i 10. jun 2022. godine",
title = "Citotoksičnost novog steroidnog bis(karbazatnog) estra, Cytotoxicity of a new steroidal bis(carbazate) ester",
pages = "93-93",
url = "https://hdl.handle.net/21.15107/rcub_cer_5783"
}

Živković, M., Novaković, I., Matić, I., Sladić, D.,& Krstić, N.. (2022). Citotoksičnost novog steroidnog bis(karbazatnog) estra. in Book of Abstracts, Proceedings - 58th Meeting of the Serbian Chemical Society, Belgrade, Serbia, June 9-10, 2022 / Kratki izvodi radova, kjniga radova - 58. Savetovanje Srpskog hemijskog društva, Beograd 9. i 10. jun 2022. godine
Belgrade: Serbian Chemical Society., 93-93.
https://hdl.handle.net/21.15107/rcub_cer_5783

Živković M, Novaković I, Matić I, Sladić D, Krstić N. Citotoksičnost novog steroidnog bis(karbazatnog) estra. in Book of Abstracts, Proceedings - 58th Meeting of the Serbian Chemical Society, Belgrade, Serbia, June 9-10, 2022 / Kratki izvodi radova, kjniga radova - 58. Savetovanje Srpskog hemijskog društva, Beograd 9. i 10. jun 2022. godine. 2022;:93-93.
https://hdl.handle.net/21.15107/rcub_cer_5783 .

Živković, Marijana, Novaković, Irena, Matić, Ivana, Sladić, Dušan, Krstić, Natalija, "Citotoksičnost novog steroidnog bis(karbazatnog) estra" in Book of Abstracts, Proceedings - 58th Meeting of the Serbian Chemical Society, Belgrade, Serbia, June 9-10, 2022 / Kratki izvodi radova, kjniga radova - 58. Savetovanje Srpskog hemijskog društva, Beograd 9. i 10. jun 2022. godine (2022):93-93,
https://hdl.handle.net/21.15107/rcub_cer_5783 .

TY  - JOUR
AU  - Čobeljić, Božidar
AU  - Živković, Marijana
AU  - Matić, Ivana
AU  - Novaković, Irena
AU  - Sladić, Dusan
AU  - Anđelković, Katarina
AU  - Krstić, Natalija
PY  - 2021
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/4912
AB  - In this work, Pt(II) complexes of previously synthesized steroidal thiosemicarbazones were synthesized and characterized. The ligands and their metal complexes were studied by analytical and spectroscopic data (elemental analysis, IR, 1D NMR and 2D NMR, HSQC, HMBC, NOESY, COSY), the analysis of which enabled complete 1H and 13C assignments of each compound including E and Z isomers. All the synthesized ligands and complexes were screened for their cytotoxic and antimicrobial activity. The results demonstrate that new steroidal thiosemicarbazone complexes were significantly less cytotoxic than corresponding steroidal thiosemicarbazones. Also, complexes show lower antimicrobial activity than the standard drugs, similar to the activity of the starting thiosemicarbazones.
AB  - Почевши од претходно синтетисаних стероидних тиосемикарбазона, у овом раду су синтетисани и окарактерисани комплекси платине(II). Лиганди и њихови метални комплекси проучавани су аналитичким и спектроскопским методама (елементална анализа, ИЦ, 1D NMR и 2D NMR, HSQC, HMBC, NOESY, COSY). Анализом добијених података омогућена је потпуна 1H и 13C асигнација свих једињења укључујући Е и Z изомере. За синтетисане лиганде, као и њихове комплексе испитивана је цитотоксична и антимикробна активност. Резултати указују на то да нови стероидни тиосемикарбазонски комплекси испољавају значајно нижу цитотоксичност од одговарајућих стероидних тиосемикарбазона. Поред тога, комплекси поседују антимикробну активност сличну активности полазних тиосемикарбазона, a нижу од стандардних лекова
PB  - Belgrade : Serbian Chemical Society
T2  - Journal of the Serbian Chemical Society
T1  - Synthesis, characterization and biological activity of Pt(II) complexes with steroidal thiosemicarbazones
T1  - Синтеза, карактеризација и биолошка активност комплекса Pt(II) са стероидним тиосемикарбазонима
VL  - 86
IS  - 5
SP  - 459
EP  - 468
DO  - 10.2298/JSC201211083C
ER  - 

@article{
author = "Čobeljić, Božidar and Živković, Marijana and Matić, Ivana and Novaković, Irena and Sladić, Dusan and Anđelković, Katarina and Krstić, Natalija",
year = "2021",
abstract = "In this work, Pt(II) complexes of previously synthesized steroidal thiosemicarbazones were synthesized and characterized. The ligands and their metal complexes were studied by analytical and spectroscopic data (elemental analysis, IR, 1D NMR and 2D NMR, HSQC, HMBC, NOESY, COSY), the analysis of which enabled complete 1H and 13C assignments of each compound including E and Z isomers. All the synthesized ligands and complexes were screened for their cytotoxic and antimicrobial activity. The results demonstrate that new steroidal thiosemicarbazone complexes were significantly less cytotoxic than corresponding steroidal thiosemicarbazones. Also, complexes show lower antimicrobial activity than the standard drugs, similar to the activity of the starting thiosemicarbazones., Почевши од претходно синтетисаних стероидних тиосемикарбазона, у овом раду су синтетисани и окарактерисани комплекси платине(II). Лиганди и њихови метални комплекси проучавани су аналитичким и спектроскопским методама (елементална анализа, ИЦ, 1D NMR и 2D NMR, HSQC, HMBC, NOESY, COSY). Анализом добијених података омогућена је потпуна 1H и 13C асигнација свих једињења укључујући Е и Z изомере. За синтетисане лиганде, као и њихове комплексе испитивана је цитотоксична и антимикробна активност. Резултати указују на то да нови стероидни тиосемикарбазонски комплекси испољавају значајно нижу цитотоксичност од одговарајућих стероидних тиосемикарбазона. Поред тога, комплекси поседују антимикробну активност сличну активности полазних тиосемикарбазона, a нижу од стандардних лекова",
publisher = "Belgrade : Serbian Chemical Society",
journal = "Journal of the Serbian Chemical Society",
title = "Synthesis, characterization and biological activity of Pt(II) complexes with steroidal thiosemicarbazones, Синтеза, карактеризација и биолошка активност комплекса Pt(II) са стероидним тиосемикарбазонима",
volume = "86",
number = "5",
pages = "459-468",
doi = "10.2298/JSC201211083C"
}

Čobeljić, B., Živković, M., Matić, I., Novaković, I., Sladić, D., Anđelković, K.,& Krstić, N.. (2021). Synthesis, characterization and biological activity of Pt(II) complexes with steroidal thiosemicarbazones. in Journal of the Serbian Chemical Society
Belgrade : Serbian Chemical Society., 86(5), 459-468.
https://doi.org/10.2298/JSC201211083C

Čobeljić B, Živković M, Matić I, Novaković I, Sladić D, Anđelković K, Krstić N. Synthesis, characterization and biological activity of Pt(II) complexes with steroidal thiosemicarbazones. in Journal of the Serbian Chemical Society. 2021;86(5):459-468.
doi:10.2298/JSC201211083C .

Čobeljić, Božidar, Živković, Marijana, Matić, Ivana, Novaković, Irena, Sladić, Dusan, Anđelković, Katarina, Krstić, Natalija, "Synthesis, characterization and biological activity of Pt(II) complexes with steroidal thiosemicarbazones" in Journal of the Serbian Chemical Society, 86, no. 5 (2021):459-468,
https://doi.org/10.2298/JSC201211083C . .

TY  - JOUR
AU  - Čobeljić, Božidar
AU  - Živković, Marijana
AU  - Matić, Ivana
AU  - Novaković, Irena
AU  - Sladić, Dusan
AU  - Anđelković, Katarina
AU  - Krstić, Natalija
PY  - 2021
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/4034
AB  - In this work, Pt(II) complexes of previously synthesized steroidal thiosemicarbazones were synthesized and characterized. The ligands and their metal complexes were studied by analytical and spectroscopic data (elemental analysis, IR, 1D NMR and 2D NMR, HSQC, HMBC, NOESY, COSY), the analysis of which enabled complete 1H and 13C assignments of each compound including E and Z isomers. All the synthesized ligands and complexes were screened for their cytotoxic and antimicrobial activity. The results demonstrate that new steroidal thiosemicarbazone complexes were significantly less cytotoxic than corresponding steroidal thiosemicarbazones. Also, complexes show lower antimicrobial activity than the standard drugs, similar to the activity of the starting thiosemicarbazones.
AB  - Почевши од претходно синтетисаних стероидних тиосемикарбазона, у овом раду су синтетисани и окарактерисани комплекси платине(II). Лиганди и њихови метални комплекси проучавани су аналитичким и спектроскопским методама (елементална анализа, ИЦ, 1D NMR и 2D NMR, HSQC, HMBC, NOESY, COSY). Анализом добијених података омогућена је потпуна 1H и 13C асигнација свих једињења укључујући Е и Z изомере. За синтетисане лиганде, као и њихове комплексе испитивана је цитотоксична и антимикробна активност. Резултати указују на то да нови стероидни тиосемикарбазонски комплекси испољавају значајно нижу цитотоксичност од одговарајућих стероидних тиосемикарбазона. Поред тога, комплекси поседују антимикробну активност сличну активности полазних тиосемикарбазона, a нижу од стандардних лекова
PB  - Belgrade : Serbian Chemical Society
T2  - Journal of the Serbian Chemical Society
T1  - Synthesis, characterization and biological activity of Pt(II) complexes with steroidal thiosemicarbazones
T1  - Синтеза, карактеризација и биолошка активност комплекса Pt(II) са стероидним тиосемикарбазонима
DO  - 10.2298/JSC201211083C
ER  - 

@article{
author = "Čobeljić, Božidar and Živković, Marijana and Matić, Ivana and Novaković, Irena and Sladić, Dusan and Anđelković, Katarina and Krstić, Natalija",
year = "2021",
abstract = "In this work, Pt(II) complexes of previously synthesized steroidal thiosemicarbazones were synthesized and characterized. The ligands and their metal complexes were studied by analytical and spectroscopic data (elemental analysis, IR, 1D NMR and 2D NMR, HSQC, HMBC, NOESY, COSY), the analysis of which enabled complete 1H and 13C assignments of each compound including E and Z isomers. All the synthesized ligands and complexes were screened for their cytotoxic and antimicrobial activity. The results demonstrate that new steroidal thiosemicarbazone complexes were significantly less cytotoxic than corresponding steroidal thiosemicarbazones. Also, complexes show lower antimicrobial activity than the standard drugs, similar to the activity of the starting thiosemicarbazones., Почевши од претходно синтетисаних стероидних тиосемикарбазона, у овом раду су синтетисани и окарактерисани комплекси платине(II). Лиганди и њихови метални комплекси проучавани су аналитичким и спектроскопским методама (елементална анализа, ИЦ, 1D NMR и 2D NMR, HSQC, HMBC, NOESY, COSY). Анализом добијених података омогућена је потпуна 1H и 13C асигнација свих једињења укључујући Е и Z изомере. За синтетисане лиганде, као и њихове комплексе испитивана је цитотоксична и антимикробна активност. Резултати указују на то да нови стероидни тиосемикарбазонски комплекси испољавају значајно нижу цитотоксичност од одговарајућих стероидних тиосемикарбазона. Поред тога, комплекси поседују антимикробну активност сличну активности полазних тиосемикарбазона, a нижу од стандардних лекова",
publisher = "Belgrade : Serbian Chemical Society",
journal = "Journal of the Serbian Chemical Society",
title = "Synthesis, characterization and biological activity of Pt(II) complexes with steroidal thiosemicarbazones, Синтеза, карактеризација и биолошка активност комплекса Pt(II) са стероидним тиосемикарбазонима",
doi = "10.2298/JSC201211083C"
}

Čobeljić, B., Živković, M., Matić, I., Novaković, I., Sladić, D., Anđelković, K.,& Krstić, N.. (2021). Synthesis, characterization and biological activity of Pt(II) complexes with steroidal thiosemicarbazones. in Journal of the Serbian Chemical Society
Belgrade : Serbian Chemical Society..
https://doi.org/10.2298/JSC201211083C

Čobeljić B, Živković M, Matić I, Novaković I, Sladić D, Anđelković K, Krstić N. Synthesis, characterization and biological activity of Pt(II) complexes with steroidal thiosemicarbazones. in Journal of the Serbian Chemical Society. 2021;.
doi:10.2298/JSC201211083C .

Čobeljić, Božidar, Živković, Marijana, Matić, Ivana, Novaković, Irena, Sladić, Dusan, Anđelković, Katarina, Krstić, Natalija, "Synthesis, characterization and biological activity of Pt(II) complexes with steroidal thiosemicarbazones" in Journal of the Serbian Chemical Society (2021),
https://doi.org/10.2298/JSC201211083C . .

TY  - JOUR
AU  - Živković, Marijana B.
AU  - Novaković, Irena
AU  - Matić, Ivana Z.
AU  - Sladić, Dušan
AU  - Krstić, Natalija
PY  - 2019
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/2947
AB  - Eleven new steroidal mono- and bis(semicarbazones) 2a–e, 4d and 3a–e have been prepared starting from various 3-oxo-α,β-unsaturated steroids. Mono-semicarbazones 2a–e were further subjected to ethyl chloroacetate in boiling absolute ethanol but, instead of expected intramolecular cyclocondensation reaction products, the new carbazate esters 5a-e were obtained. The structures of all synthesized compounds and identification of each E/Z isomer were deduced by elemental analysis, HRMS, NMR, and IR spectroscopy. Preliminary screening for the cytotoxic activity in vitro of the new compounds has been conducted against three cancer cell lines, K562, Jurkat and HeLa cells. HeLa cells were the most sensitive while K562 cells were the least sensitive to the cytotoxic action of the novel steroid derivatives. Compounds 2e, 3c and 5e were found to have the best but still moderate cytotoxic effects. All tested compounds showed very weak antimicrobial activities. These results demonstrate that the replacement of thioxo group with carbonyl group in steroidal hydrazone derivatives resulted in decrease in their biological activity.
PB  - Elsevier
T2  - Steroids
T1  - Synthesis and preliminary screening for the biological activity of some steroidal Δ4-unsaturated semicarbazone derivatives
VL  - 148
SP  - 36
EP  - 46
DO  - 10.1016/j.steroids.2019.04.010
ER  - 

@article{
author = "Živković, Marijana B. and Novaković, Irena and Matić, Ivana Z. and Sladić, Dušan and Krstić, Natalija",
year = "2019",
abstract = "Eleven new steroidal mono- and bis(semicarbazones) 2a–e, 4d and 3a–e have been prepared starting from various 3-oxo-α,β-unsaturated steroids. Mono-semicarbazones 2a–e were further subjected to ethyl chloroacetate in boiling absolute ethanol but, instead of expected intramolecular cyclocondensation reaction products, the new carbazate esters 5a-e were obtained. The structures of all synthesized compounds and identification of each E/Z isomer were deduced by elemental analysis, HRMS, NMR, and IR spectroscopy. Preliminary screening for the cytotoxic activity in vitro of the new compounds has been conducted against three cancer cell lines, K562, Jurkat and HeLa cells. HeLa cells were the most sensitive while K562 cells were the least sensitive to the cytotoxic action of the novel steroid derivatives. Compounds 2e, 3c and 5e were found to have the best but still moderate cytotoxic effects. All tested compounds showed very weak antimicrobial activities. These results demonstrate that the replacement of thioxo group with carbonyl group in steroidal hydrazone derivatives resulted in decrease in their biological activity.",
publisher = "Elsevier",
journal = "Steroids",
title = "Synthesis and preliminary screening for the biological activity of some steroidal Δ4-unsaturated semicarbazone derivatives",
volume = "148",
pages = "36-46",
doi = "10.1016/j.steroids.2019.04.010"
}

Živković, M. B., Novaković, I., Matić, I. Z., Sladić, D.,& Krstić, N.. (2019). Synthesis and preliminary screening for the biological activity of some steroidal Δ4-unsaturated semicarbazone derivatives. in Steroids
Elsevier., 148, 36-46.
https://doi.org/10.1016/j.steroids.2019.04.010

Živković MB, Novaković I, Matić IZ, Sladić D, Krstić N. Synthesis and preliminary screening for the biological activity of some steroidal Δ4-unsaturated semicarbazone derivatives. in Steroids. 2019;148:36-46.
doi:10.1016/j.steroids.2019.04.010 .

Živković, Marijana B., Novaković, Irena, Matić, Ivana Z., Sladić, Dušan, Krstić, Natalija, "Synthesis and preliminary screening for the biological activity of some steroidal Δ4-unsaturated semicarbazone derivatives" in Steroids, 148 (2019):36-46,
https://doi.org/10.1016/j.steroids.2019.04.010 . .

TY  - JOUR
AU  - Živković, Marijana B.
AU  - Novaković, Irena
AU  - Matić, Ivana Z.
AU  - Sladić, Dušan
AU  - Krstić, Natalija
PY  - 2019
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/2948
AB  - Eleven new steroidal mono- and bis(semicarbazones) 2a–e, 4d and 3a–e have been prepared starting from various 3-oxo-α,β-unsaturated steroids. Mono-semicarbazones 2a–e were further subjected to ethyl chloroacetate in boiling absolute ethanol but, instead of expected intramolecular cyclocondensation reaction products, the new carbazate esters 5a-e were obtained. The structures of all synthesized compounds and identification of each E/Z isomer were deduced by elemental analysis, HRMS, NMR, and IR spectroscopy. Preliminary screening for the cytotoxic activity in vitro of the new compounds has been conducted against three cancer cell lines, K562, Jurkat and HeLa cells. HeLa cells were the most sensitive while K562 cells were the least sensitive to the cytotoxic action of the novel steroid derivatives. Compounds 2e, 3c and 5e were found to have the best but still moderate cytotoxic effects. All tested compounds showed very weak antimicrobial activities. These results demonstrate that the replacement of thioxo group with carbonyl group in steroidal hydrazone derivatives resulted in decrease in their biological activity.
PB  - Elsevier
T2  - Steroids
T1  - Synthesis and preliminary screening for the biological activity of some steroidal Δ4-unsaturated semicarbazone derivatives
VL  - 148
SP  - 36
EP  - 46
DO  - 10.1016/j.steroids.2019.04.010
ER  - 

@article{
author = "Živković, Marijana B. and Novaković, Irena and Matić, Ivana Z. and Sladić, Dušan and Krstić, Natalija",
year = "2019",
abstract = "Eleven new steroidal mono- and bis(semicarbazones) 2a–e, 4d and 3a–e have been prepared starting from various 3-oxo-α,β-unsaturated steroids. Mono-semicarbazones 2a–e were further subjected to ethyl chloroacetate in boiling absolute ethanol but, instead of expected intramolecular cyclocondensation reaction products, the new carbazate esters 5a-e were obtained. The structures of all synthesized compounds and identification of each E/Z isomer were deduced by elemental analysis, HRMS, NMR, and IR spectroscopy. Preliminary screening for the cytotoxic activity in vitro of the new compounds has been conducted against three cancer cell lines, K562, Jurkat and HeLa cells. HeLa cells were the most sensitive while K562 cells were the least sensitive to the cytotoxic action of the novel steroid derivatives. Compounds 2e, 3c and 5e were found to have the best but still moderate cytotoxic effects. All tested compounds showed very weak antimicrobial activities. These results demonstrate that the replacement of thioxo group with carbonyl group in steroidal hydrazone derivatives resulted in decrease in their biological activity.",
publisher = "Elsevier",
journal = "Steroids",
title = "Synthesis and preliminary screening for the biological activity of some steroidal Δ4-unsaturated semicarbazone derivatives",
volume = "148",
pages = "36-46",
doi = "10.1016/j.steroids.2019.04.010"
}

Živković, M. B., Novaković, I., Matić, I. Z., Sladić, D.,& Krstić, N.. (2019). Synthesis and preliminary screening for the biological activity of some steroidal Δ4-unsaturated semicarbazone derivatives. in Steroids
Elsevier., 148, 36-46.
https://doi.org/10.1016/j.steroids.2019.04.010

Živković MB, Novaković I, Matić IZ, Sladić D, Krstić N. Synthesis and preliminary screening for the biological activity of some steroidal Δ4-unsaturated semicarbazone derivatives. in Steroids. 2019;148:36-46.
doi:10.1016/j.steroids.2019.04.010 .

Živković, Marijana B., Novaković, Irena, Matić, Ivana Z., Sladić, Dušan, Krstić, Natalija, "Synthesis and preliminary screening for the biological activity of some steroidal Δ4-unsaturated semicarbazone derivatives" in Steroids, 148 (2019):36-46,
https://doi.org/10.1016/j.steroids.2019.04.010 . .

TY  - JOUR
AU  - Živković, Marijana
AU  - Matić, Ivana Z.
AU  - Rodić, Marko V.
AU  - Novaković, Irena
AU  - Krivokuca, Ana M.
AU  - Sladić, Dušan
AU  - Krstić, Natalija
PY  - 2017
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/2089
AB  - The synthesis and cytotoxic activities determination of new steroidal mono- and bis(thiazolidin-4-ones) 4a-f and 5a-f have been performed. Their anticancer action was also evaluated in comparison to previously synthesized and reported corresponding steroidal thiosemicarbazones. All compounds were obtained as stereoisomeric mixtures with different configuration (E or Z) in the hydrazone moiety at the C-3 position. After several consecutive crystallizations diastereomerically pure major (5)-isomers of mono-thiazolidin-4-ones were isolated. The structure and stereochemistry of 2,4-thiazolidinedione,2-[(17-oxoandrost-4-en-3-ylidene)hydrazone] were confirmed by X-ray analysis. A pathway for the formation of thiazolidin-4-one ring was proposed. The steroid thiazolidinone derivatives examined in this study exerted selective concentration-dependent cytotoxic activities on six tested malignant cell lines. Ten out of twelve examined compounds exhibited strong cytotoxic effects on K562 cells (IC50 values from 8.5 mu M to 14.9 mu M), eight on HeLa cells (IC50 values ranging from 8.9 mu M to 15.1 mu M) while against MDA-MB-361 cells six compouds exerted similar or even higher cytotoxic action (IC50 values from 12.7 mu M to 25.6 mu M) than cisplatin (21.5 mu M) which served as a positive control. Eight of these ten compounds showed high selectivity in the cytotoxic action against HeLa and K562 cancer cell lines when compared with normal human fibroblasts MRC-5 and normal human PBMC. The study of mechanisms of the anticancer activity of the two selected compounds, mono- and bis(thiazolidin-4-one) derivatives of 19-norandrost-4-ene-3,17-dione 4a and 5a, revealed that both of these compounds induced apoptosis in HeLa cells through extrinsic and intrinsic signalling pathways. Treatment of EA.hy926 cells with sub-toxic concentrations of these compounds led to the inhibition of cell connecting and sprouting, and tube formation. The synthesized compounds exhibited poor antioxidant activity.
PB  - Oxford : Pergamon-Elsevier Science Ltd
T2  - Journal of Steroid Biochemistry and Molecular Biology
T1  - Anticancer potential of new steroidal thiazolidin-4-one derivatives. Mechanisms of cytotoxic action and effects on angiogenesis in vitro
VL  - 174
SP  - 72
EP  - 85
DO  - 10.1016/j.jsbmb.2017.07.031
ER  - 

@article{
author = "Živković, Marijana and Matić, Ivana Z. and Rodić, Marko V. and Novaković, Irena and Krivokuca, Ana M. and Sladić, Dušan and Krstić, Natalija",
year = "2017",
abstract = "The synthesis and cytotoxic activities determination of new steroidal mono- and bis(thiazolidin-4-ones) 4a-f and 5a-f have been performed. Their anticancer action was also evaluated in comparison to previously synthesized and reported corresponding steroidal thiosemicarbazones. All compounds were obtained as stereoisomeric mixtures with different configuration (E or Z) in the hydrazone moiety at the C-3 position. After several consecutive crystallizations diastereomerically pure major (5)-isomers of mono-thiazolidin-4-ones were isolated. The structure and stereochemistry of 2,4-thiazolidinedione,2-[(17-oxoandrost-4-en-3-ylidene)hydrazone] were confirmed by X-ray analysis. A pathway for the formation of thiazolidin-4-one ring was proposed. The steroid thiazolidinone derivatives examined in this study exerted selective concentration-dependent cytotoxic activities on six tested malignant cell lines. Ten out of twelve examined compounds exhibited strong cytotoxic effects on K562 cells (IC50 values from 8.5 mu M to 14.9 mu M), eight on HeLa cells (IC50 values ranging from 8.9 mu M to 15.1 mu M) while against MDA-MB-361 cells six compouds exerted similar or even higher cytotoxic action (IC50 values from 12.7 mu M to 25.6 mu M) than cisplatin (21.5 mu M) which served as a positive control. Eight of these ten compounds showed high selectivity in the cytotoxic action against HeLa and K562 cancer cell lines when compared with normal human fibroblasts MRC-5 and normal human PBMC. The study of mechanisms of the anticancer activity of the two selected compounds, mono- and bis(thiazolidin-4-one) derivatives of 19-norandrost-4-ene-3,17-dione 4a and 5a, revealed that both of these compounds induced apoptosis in HeLa cells through extrinsic and intrinsic signalling pathways. Treatment of EA.hy926 cells with sub-toxic concentrations of these compounds led to the inhibition of cell connecting and sprouting, and tube formation. The synthesized compounds exhibited poor antioxidant activity.",
publisher = "Oxford : Pergamon-Elsevier Science Ltd",
journal = "Journal of Steroid Biochemistry and Molecular Biology",
title = "Anticancer potential of new steroidal thiazolidin-4-one derivatives. Mechanisms of cytotoxic action and effects on angiogenesis in vitro",
volume = "174",
pages = "72-85",
doi = "10.1016/j.jsbmb.2017.07.031"
}

Živković, M., Matić, I. Z., Rodić, M. V., Novaković, I., Krivokuca, A. M., Sladić, D.,& Krstić, N.. (2017). Anticancer potential of new steroidal thiazolidin-4-one derivatives. Mechanisms of cytotoxic action and effects on angiogenesis in vitro. in Journal of Steroid Biochemistry and Molecular Biology
Oxford : Pergamon-Elsevier Science Ltd., 174, 72-85.
https://doi.org/10.1016/j.jsbmb.2017.07.031

Živković M, Matić IZ, Rodić MV, Novaković I, Krivokuca AM, Sladić D, Krstić N. Anticancer potential of new steroidal thiazolidin-4-one derivatives. Mechanisms of cytotoxic action and effects on angiogenesis in vitro. in Journal of Steroid Biochemistry and Molecular Biology. 2017;174:72-85.
doi:10.1016/j.jsbmb.2017.07.031 .

Živković, Marijana, Matić, Ivana Z., Rodić, Marko V., Novaković, Irena, Krivokuca, Ana M., Sladić, Dušan, Krstić, Natalija, "Anticancer potential of new steroidal thiazolidin-4-one derivatives. Mechanisms of cytotoxic action and effects on angiogenesis in vitro" in Journal of Steroid Biochemistry and Molecular Biology, 174 (2017):72-85,
https://doi.org/10.1016/j.jsbmb.2017.07.031 . .

TY  - JOUR
AU  - Živković, Marijana
AU  - Matić, Ivana Z.
AU  - Rodić, Marko V.
AU  - Novaković, Irena
AU  - Krivokuca, Ana M.
AU  - Sladić, Dušan
AU  - Krstić, Natalija
PY  - 2017
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/3009
AB  - The synthesis and cytotoxic activities determination of new steroidal mono- and bis(thiazolidin-4-ones) 4a-f and 5a-f have been performed. Their anticancer action was also evaluated in comparison to previously synthesized and reported corresponding steroidal thiosemicarbazones. All compounds were obtained as stereoisomeric mixtures with different configuration (E or Z) in the hydrazone moiety at the C-3 position. After several consecutive crystallizations diastereomerically pure major (5)-isomers of mono-thiazolidin-4-ones were isolated. The structure and stereochemistry of 2,4-thiazolidinedione,2-[(17-oxoandrost-4-en-3-ylidene)hydrazone] were confirmed by X-ray analysis. A pathway for the formation of thiazolidin-4-one ring was proposed. The steroid thiazolidinone derivatives examined in this study exerted selective concentration-dependent cytotoxic activities on six tested malignant cell lines. Ten out of twelve examined compounds exhibited strong cytotoxic effects on K562 cells (IC50 values from 8.5 mu M to 14.9 mu M), eight on HeLa cells (IC50 values ranging from 8.9 mu M to 15.1 mu M) while against MDA-MB-361 cells six compouds exerted similar or even higher cytotoxic action (IC50 values from 12.7 mu M to 25.6 mu M) than cisplatin (21.5 mu M) which served as a positive control. Eight of these ten compounds showed high selectivity in the cytotoxic action against HeLa and K562 cancer cell lines when compared with normal human fibroblasts MRC-5 and normal human PBMC. The study of mechanisms of the anticancer activity of the two selected compounds, mono- and bis(thiazolidin-4-one) derivatives of 19-norandrost-4-ene-3,17-dione 4a and 5a, revealed that both of these compounds induced apoptosis in HeLa cells through extrinsic and intrinsic signalling pathways. Treatment of EA.hy926 cells with sub-toxic concentrations of these compounds led to the inhibition of cell connecting and sprouting, and tube formation. The synthesized compounds exhibited poor antioxidant activity.
PB  - Oxford : Pergamon-Elsevier Science Ltd
T2  - Journal of Steroid Biochemistry and Molecular Biology
T1  - Anticancer potential of new steroidal thiazolidin-4-one derivatives. Mechanisms of cytotoxic action and effects on angiogenesis in vitro
VL  - 174
SP  - 72
EP  - 85
DO  - 10.1016/j.jsbmb.2017.07.031
ER  - 

@article{
author = "Živković, Marijana and Matić, Ivana Z. and Rodić, Marko V. and Novaković, Irena and Krivokuca, Ana M. and Sladić, Dušan and Krstić, Natalija",
year = "2017",
abstract = "The synthesis and cytotoxic activities determination of new steroidal mono- and bis(thiazolidin-4-ones) 4a-f and 5a-f have been performed. Their anticancer action was also evaluated in comparison to previously synthesized and reported corresponding steroidal thiosemicarbazones. All compounds were obtained as stereoisomeric mixtures with different configuration (E or Z) in the hydrazone moiety at the C-3 position. After several consecutive crystallizations diastereomerically pure major (5)-isomers of mono-thiazolidin-4-ones were isolated. The structure and stereochemistry of 2,4-thiazolidinedione,2-[(17-oxoandrost-4-en-3-ylidene)hydrazone] were confirmed by X-ray analysis. A pathway for the formation of thiazolidin-4-one ring was proposed. The steroid thiazolidinone derivatives examined in this study exerted selective concentration-dependent cytotoxic activities on six tested malignant cell lines. Ten out of twelve examined compounds exhibited strong cytotoxic effects on K562 cells (IC50 values from 8.5 mu M to 14.9 mu M), eight on HeLa cells (IC50 values ranging from 8.9 mu M to 15.1 mu M) while against MDA-MB-361 cells six compouds exerted similar or even higher cytotoxic action (IC50 values from 12.7 mu M to 25.6 mu M) than cisplatin (21.5 mu M) which served as a positive control. Eight of these ten compounds showed high selectivity in the cytotoxic action against HeLa and K562 cancer cell lines when compared with normal human fibroblasts MRC-5 and normal human PBMC. The study of mechanisms of the anticancer activity of the two selected compounds, mono- and bis(thiazolidin-4-one) derivatives of 19-norandrost-4-ene-3,17-dione 4a and 5a, revealed that both of these compounds induced apoptosis in HeLa cells through extrinsic and intrinsic signalling pathways. Treatment of EA.hy926 cells with sub-toxic concentrations of these compounds led to the inhibition of cell connecting and sprouting, and tube formation. The synthesized compounds exhibited poor antioxidant activity.",
publisher = "Oxford : Pergamon-Elsevier Science Ltd",
journal = "Journal of Steroid Biochemistry and Molecular Biology",
title = "Anticancer potential of new steroidal thiazolidin-4-one derivatives. Mechanisms of cytotoxic action and effects on angiogenesis in vitro",
volume = "174",
pages = "72-85",
doi = "10.1016/j.jsbmb.2017.07.031"
}

Živković, M., Matić, I. Z., Rodić, M. V., Novaković, I., Krivokuca, A. M., Sladić, D.,& Krstić, N.. (2017). Anticancer potential of new steroidal thiazolidin-4-one derivatives. Mechanisms of cytotoxic action and effects on angiogenesis in vitro. in Journal of Steroid Biochemistry and Molecular Biology
Oxford : Pergamon-Elsevier Science Ltd., 174, 72-85.
https://doi.org/10.1016/j.jsbmb.2017.07.031

Živković M, Matić IZ, Rodić MV, Novaković I, Krivokuca AM, Sladić D, Krstić N. Anticancer potential of new steroidal thiazolidin-4-one derivatives. Mechanisms of cytotoxic action and effects on angiogenesis in vitro. in Journal of Steroid Biochemistry and Molecular Biology. 2017;174:72-85.
doi:10.1016/j.jsbmb.2017.07.031 .

Živković, Marijana, Matić, Ivana Z., Rodić, Marko V., Novaković, Irena, Krivokuca, Ana M., Sladić, Dušan, Krstić, Natalija, "Anticancer potential of new steroidal thiazolidin-4-one derivatives. Mechanisms of cytotoxic action and effects on angiogenesis in vitro" in Journal of Steroid Biochemistry and Molecular Biology, 174 (2017):72-85,
https://doi.org/10.1016/j.jsbmb.2017.07.031 . .

TY  - JOUR
AU  - Živković, Marijana
AU  - Matić, Ivana Z.
AU  - Rodić, Marko V.
AU  - Novaković, Irena
AU  - Sladić, Dušan
AU  - Krstić, Natalija
PY  - 2016
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/2028
AB  - A series of new steroidal mono- and bis(thiosemicarbazones) (2a-e and 3a-e) and corresponding mono- and bis(1,3,4-thiadiazolines) (4a-e and 5a-e) was synthesized, characterized and evaluated for their anticancer activity. Detailed NMR analysis of the mono-and bis(thiosemicarbazones) revealed the presence of two stereoisomers (Z and E) with different configurations in the hydrazone moiety at the C-3 position, where the substituents on the C(3)]=N double bond in the main isomers adopted the E configuration. The configurations at C-3 and C-17 in thiadiazolines 4a-e and 5a-e were deduced by detailed NMR analysis as well as by the examination of Dreiding molecular models and X-ray analysis of 3-thiadiazoline 4a, which confirmed the structure and absolute configuration at C-3. The synthesized compounds were tested against six cancer cell lines (HeLa, K562, MDA-MB-361, MDA-MB-453, LS174 and A549), the normal human cell line MRC-5 and peripheral blood mononuclear cells (PBMC) isolated from healthy donors. The best activity was exhibited by 3-thiosemicarbazones 2a, 2b, 2c and 2e and 3,17-bis(thiadiazolines) 5a and 5d. Examination of the mechanisms of cytotoxicity on cervical adenocarcinoma HeLa cells revealed the pro-apoptotic action of these compounds, which triggered both extrinsic and intrinsic apoptotic pathways. These compounds also showed the ability to decrease angiogenesis in vitro. In addition, 3,17-bis(thiadiazolines) 5a and 5d showed high selectivity in anticancer activity against all the examined malignant cell lines. Compound 5a displayed prominent anticancer potential. The tested compounds showed poor antimicrobial activity.
PB  - Royal Soc Chemistry, Cambridge
T2  - RSC Advances
T1  - Synthesis, characterization and in vitro cytotoxic activities of new steroidal thiosemicarbazones and thiadiazolines
VL  - 6
IS  - 41
SP  - 34312
EP  - 34333
DO  - 10.1039/c6ra01516f
ER  - 

@article{
author = "Živković, Marijana and Matić, Ivana Z. and Rodić, Marko V. and Novaković, Irena and Sladić, Dušan and Krstić, Natalija",
year = "2016",
abstract = "A series of new steroidal mono- and bis(thiosemicarbazones) (2a-e and 3a-e) and corresponding mono- and bis(1,3,4-thiadiazolines) (4a-e and 5a-e) was synthesized, characterized and evaluated for their anticancer activity. Detailed NMR analysis of the mono-and bis(thiosemicarbazones) revealed the presence of two stereoisomers (Z and E) with different configurations in the hydrazone moiety at the C-3 position, where the substituents on the C(3)]=N double bond in the main isomers adopted the E configuration. The configurations at C-3 and C-17 in thiadiazolines 4a-e and 5a-e were deduced by detailed NMR analysis as well as by the examination of Dreiding molecular models and X-ray analysis of 3-thiadiazoline 4a, which confirmed the structure and absolute configuration at C-3. The synthesized compounds were tested against six cancer cell lines (HeLa, K562, MDA-MB-361, MDA-MB-453, LS174 and A549), the normal human cell line MRC-5 and peripheral blood mononuclear cells (PBMC) isolated from healthy donors. The best activity was exhibited by 3-thiosemicarbazones 2a, 2b, 2c and 2e and 3,17-bis(thiadiazolines) 5a and 5d. Examination of the mechanisms of cytotoxicity on cervical adenocarcinoma HeLa cells revealed the pro-apoptotic action of these compounds, which triggered both extrinsic and intrinsic apoptotic pathways. These compounds also showed the ability to decrease angiogenesis in vitro. In addition, 3,17-bis(thiadiazolines) 5a and 5d showed high selectivity in anticancer activity against all the examined malignant cell lines. Compound 5a displayed prominent anticancer potential. The tested compounds showed poor antimicrobial activity.",
publisher = "Royal Soc Chemistry, Cambridge",
journal = "RSC Advances",
title = "Synthesis, characterization and in vitro cytotoxic activities of new steroidal thiosemicarbazones and thiadiazolines",
volume = "6",
number = "41",
pages = "34312-34333",
doi = "10.1039/c6ra01516f"
}

Živković, M., Matić, I. Z., Rodić, M. V., Novaković, I., Sladić, D.,& Krstić, N.. (2016). Synthesis, characterization and in vitro cytotoxic activities of new steroidal thiosemicarbazones and thiadiazolines. in RSC Advances
Royal Soc Chemistry, Cambridge., 6(41), 34312-34333.
https://doi.org/10.1039/c6ra01516f

Živković M, Matić IZ, Rodić MV, Novaković I, Sladić D, Krstić N. Synthesis, characterization and in vitro cytotoxic activities of new steroidal thiosemicarbazones and thiadiazolines. in RSC Advances. 2016;6(41):34312-34333.
doi:10.1039/c6ra01516f .

Živković, Marijana, Matić, Ivana Z., Rodić, Marko V., Novaković, Irena, Sladić, Dušan, Krstić, Natalija, "Synthesis, characterization and in vitro cytotoxic activities of new steroidal thiosemicarbazones and thiadiazolines" in RSC Advances, 6, no. 41 (2016):34312-34333,
https://doi.org/10.1039/c6ra01516f . .

TY  - JOUR
AU  - Milenković, Milica R.
AU  - Pevec, Andrej
AU  - Turel, Iztok
AU  - Milenković, Marina
AU  - Čobeljić, Božidar
AU  - Sladić, Dušan
AU  - Krstić, Natalija
AU  - Anđelković, Katarina
PY  - 2015
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/3123
AB  - Square-planar isocyanate and chloride Ni(II) complexes with tridentate PNO condensation product of 2-(diphenylphosphino)benzaldehyde and Girard's T reagent have been synthesized and their crystal structures were determined. These Ni(II) complexes with different monodentate ligands, chloride, cyanate, and thiocyanate were tested for their antimicrobial activities against pathogenic microorganisms. The ligand and Ni(II) complexes were active not only against laboratory control strains of bacteria and yeast, but also on clinical isolates of Escherichia coli and Pseudomonas aeruginosa strains resistant to most of the clinically used antibiotics.
PB  - Taylor & Francis Ltd, Abingdon
T2  - Journal of Coordination Chemistry
T1  - Synthesis, crystal structures, and antimicrobial activity of square-planar chloride and isocyanate Ni(II) complexes with the condensation product of 2-(diphenylphosphino)benzaldehyde and Girard's T reagent
VL  - 68
IS  - 16
SP  - 2858
EP  - 2870
DO  - 10.1080/00958972.2015.1055260
ER  - 

@article{
author = "Milenković, Milica R. and Pevec, Andrej and Turel, Iztok and Milenković, Marina and Čobeljić, Božidar and Sladić, Dušan and Krstić, Natalija and Anđelković, Katarina",
year = "2015",
abstract = "Square-planar isocyanate and chloride Ni(II) complexes with tridentate PNO condensation product of 2-(diphenylphosphino)benzaldehyde and Girard's T reagent have been synthesized and their crystal structures were determined. These Ni(II) complexes with different monodentate ligands, chloride, cyanate, and thiocyanate were tested for their antimicrobial activities against pathogenic microorganisms. The ligand and Ni(II) complexes were active not only against laboratory control strains of bacteria and yeast, but also on clinical isolates of Escherichia coli and Pseudomonas aeruginosa strains resistant to most of the clinically used antibiotics.",
publisher = "Taylor & Francis Ltd, Abingdon",
journal = "Journal of Coordination Chemistry",
title = "Synthesis, crystal structures, and antimicrobial activity of square-planar chloride and isocyanate Ni(II) complexes with the condensation product of 2-(diphenylphosphino)benzaldehyde and Girard's T reagent",
volume = "68",
number = "16",
pages = "2858-2870",
doi = "10.1080/00958972.2015.1055260"
}

Milenković, M. R., Pevec, A., Turel, I., Milenković, M., Čobeljić, B., Sladić, D., Krstić, N.,& Anđelković, K.. (2015). Synthesis, crystal structures, and antimicrobial activity of square-planar chloride and isocyanate Ni(II) complexes with the condensation product of 2-(diphenylphosphino)benzaldehyde and Girard's T reagent. in Journal of Coordination Chemistry
Taylor & Francis Ltd, Abingdon., 68(16), 2858-2870.
https://doi.org/10.1080/00958972.2015.1055260

Milenković MR, Pevec A, Turel I, Milenković M, Čobeljić B, Sladić D, Krstić N, Anđelković K. Synthesis, crystal structures, and antimicrobial activity of square-planar chloride and isocyanate Ni(II) complexes with the condensation product of 2-(diphenylphosphino)benzaldehyde and Girard's T reagent. in Journal of Coordination Chemistry. 2015;68(16):2858-2870.
doi:10.1080/00958972.2015.1055260 .

Milenković, Milica R., Pevec, Andrej, Turel, Iztok, Milenković, Marina, Čobeljić, Božidar, Sladić, Dušan, Krstić, Natalija, Anđelković, Katarina, "Synthesis, crystal structures, and antimicrobial activity of square-planar chloride and isocyanate Ni(II) complexes with the condensation product of 2-(diphenylphosphino)benzaldehyde and Girard's T reagent" in Journal of Coordination Chemistry, 68, no. 16 (2015):2858-2870,
https://doi.org/10.1080/00958972.2015.1055260 . .

TY  - JOUR
AU  - Milenković, Milica R.
AU  - Pevec, Andrej
AU  - Turel, Iztok
AU  - Milenković, Marina
AU  - Čobeljić, Božidar
AU  - Sladić, Dušan
AU  - Krstić, Natalija
AU  - Anđelković, Katarina
PY  - 2015
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/1707
AB  - Square-planar isocyanate and chloride Ni(II) complexes with tridentate PNO condensation product of 2-(diphenylphosphino)benzaldehyde and Girard's T reagent have been synthesized and their crystal structures were determined. These Ni(II) complexes with different monodentate ligands, chloride, cyanate, and thiocyanate were tested for their antimicrobial activities against pathogenic microorganisms. The ligand and Ni(II) complexes were active not only against laboratory control strains of bacteria and yeast, but also on clinical isolates of Escherichia coli and Pseudomonas aeruginosa strains resistant to most of the clinically used antibiotics.
PB  - Taylor & Francis Ltd, Abingdon
T2  - Journal of Coordination Chemistry
T1  - Synthesis, crystal structures, and antimicrobial activity of square-planar chloride and isocyanate Ni(II) complexes with the condensation product of 2-(diphenylphosphino)benzaldehyde and Girard's T reagent
VL  - 68
IS  - 16
SP  - 2858
EP  - 2870
DO  - 10.1080/00958972.2015.1055260
ER  - 

@article{
author = "Milenković, Milica R. and Pevec, Andrej and Turel, Iztok and Milenković, Marina and Čobeljić, Božidar and Sladić, Dušan and Krstić, Natalija and Anđelković, Katarina",
year = "2015",
abstract = "Square-planar isocyanate and chloride Ni(II) complexes with tridentate PNO condensation product of 2-(diphenylphosphino)benzaldehyde and Girard's T reagent have been synthesized and their crystal structures were determined. These Ni(II) complexes with different monodentate ligands, chloride, cyanate, and thiocyanate were tested for their antimicrobial activities against pathogenic microorganisms. The ligand and Ni(II) complexes were active not only against laboratory control strains of bacteria and yeast, but also on clinical isolates of Escherichia coli and Pseudomonas aeruginosa strains resistant to most of the clinically used antibiotics.",
publisher = "Taylor & Francis Ltd, Abingdon",
journal = "Journal of Coordination Chemistry",
title = "Synthesis, crystal structures, and antimicrobial activity of square-planar chloride and isocyanate Ni(II) complexes with the condensation product of 2-(diphenylphosphino)benzaldehyde and Girard's T reagent",
volume = "68",
number = "16",
pages = "2858-2870",
doi = "10.1080/00958972.2015.1055260"
}

Milenković, M. R., Pevec, A., Turel, I., Milenković, M., Čobeljić, B., Sladić, D., Krstić, N.,& Anđelković, K.. (2015). Synthesis, crystal structures, and antimicrobial activity of square-planar chloride and isocyanate Ni(II) complexes with the condensation product of 2-(diphenylphosphino)benzaldehyde and Girard's T reagent. in Journal of Coordination Chemistry
Taylor & Francis Ltd, Abingdon., 68(16), 2858-2870.
https://doi.org/10.1080/00958972.2015.1055260

Milenković MR, Pevec A, Turel I, Milenković M, Čobeljić B, Sladić D, Krstić N, Anđelković K. Synthesis, crystal structures, and antimicrobial activity of square-planar chloride and isocyanate Ni(II) complexes with the condensation product of 2-(diphenylphosphino)benzaldehyde and Girard's T reagent. in Journal of Coordination Chemistry. 2015;68(16):2858-2870.
doi:10.1080/00958972.2015.1055260 .

Milenković, Milica R., Pevec, Andrej, Turel, Iztok, Milenković, Marina, Čobeljić, Božidar, Sladić, Dušan, Krstić, Natalija, Anđelković, Katarina, "Synthesis, crystal structures, and antimicrobial activity of square-planar chloride and isocyanate Ni(II) complexes with the condensation product of 2-(diphenylphosphino)benzaldehyde and Girard's T reagent" in Journal of Coordination Chemistry, 68, no. 16 (2015):2858-2870,
https://doi.org/10.1080/00958972.2015.1055260 . .

TY  - JOUR
AU  - Krstić, Natalija
AU  - Matić, Ivana Z.
AU  - Juranić, Zorica
AU  - Novaković, Irena
AU  - Sladić, Dušan
PY  - 2014
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/1409
AB  - The in vitro cytotoxic activity of previously synthesized steroid dimers with different spacer group (sulfide, trithiolane ring or phosphorotrithioate) and the substituent at C-17 position was tested for their possible effects against following human tumor cell lines: cervical adenocarcinoma (HeLa), chronic myelogenous leukemia (K562) and two human breast cancer cell lines (MDA-MB-361 and MDA-MB-453). These compounds, applied at micromolar concentrations, exhibited cytotoxic activity of different intensity (compared with cisplatin as a control), modality and selectivity in these malignant cell lines. The best activity against all four cell cancer lines was exhibited by dimer-sulfides. All screened compounds exerted concentration-dependent cytotoxic activity against leukemia K562 cells. The compounds which exerted the most pronounced cytotoxic action exhibited notably higher cytotoxic activities against K562, HeLa and MDA-MB-453 cells in comparison to resting and PHA-stimulated PBMC, pointing to a significant selectivity in their antitumor actions. Examination of the mechanisms of cytotoxicity on leukemia K562 cells revealed pro-apoptotic action of each of the investigated compounds applied at concentrations 2IC(50). The most prominent pro-apoptotic action was exhibited by dimer-sulfide of cholest-4-en-3-one. Furthermore, almost all of the tested compounds at IC50 concentrations induced G1 phase cell cycle arrest in K562 cells. Antimicrobial activity against Gram-positive, Gram-negative bacteria and fungal cells, and toxicity to brine shrimp Artemia sauna, were evaluated. There was no antibacterial activity. The best antifungal activity was exhibited against Saccharomyces cerevisiae by dimers linked with trithiolane ring, indicating a selective activity of investigated compounds.
PB  - Oxford : Pergamon-Elsevier Science Ltd
T2  - Journal of Steroid Biochemistry and Molecular Biology
T1  - Steroid dimers-In vitro cytotoxic and antimicrobial activities
VL  - 143
SP  - 365
EP  - 375
DO  - 10.1016/j.jsbmb.2014.06.005
ER  - 

@article{
author = "Krstić, Natalija and Matić, Ivana Z. and Juranić, Zorica and Novaković, Irena and Sladić, Dušan",
year = "2014",
abstract = "The in vitro cytotoxic activity of previously synthesized steroid dimers with different spacer group (sulfide, trithiolane ring or phosphorotrithioate) and the substituent at C-17 position was tested for their possible effects against following human tumor cell lines: cervical adenocarcinoma (HeLa), chronic myelogenous leukemia (K562) and two human breast cancer cell lines (MDA-MB-361 and MDA-MB-453). These compounds, applied at micromolar concentrations, exhibited cytotoxic activity of different intensity (compared with cisplatin as a control), modality and selectivity in these malignant cell lines. The best activity against all four cell cancer lines was exhibited by dimer-sulfides. All screened compounds exerted concentration-dependent cytotoxic activity against leukemia K562 cells. The compounds which exerted the most pronounced cytotoxic action exhibited notably higher cytotoxic activities against K562, HeLa and MDA-MB-453 cells in comparison to resting and PHA-stimulated PBMC, pointing to a significant selectivity in their antitumor actions. Examination of the mechanisms of cytotoxicity on leukemia K562 cells revealed pro-apoptotic action of each of the investigated compounds applied at concentrations 2IC(50). The most prominent pro-apoptotic action was exhibited by dimer-sulfide of cholest-4-en-3-one. Furthermore, almost all of the tested compounds at IC50 concentrations induced G1 phase cell cycle arrest in K562 cells. Antimicrobial activity against Gram-positive, Gram-negative bacteria and fungal cells, and toxicity to brine shrimp Artemia sauna, were evaluated. There was no antibacterial activity. The best antifungal activity was exhibited against Saccharomyces cerevisiae by dimers linked with trithiolane ring, indicating a selective activity of investigated compounds.",
publisher = "Oxford : Pergamon-Elsevier Science Ltd",
journal = "Journal of Steroid Biochemistry and Molecular Biology",
title = "Steroid dimers-In vitro cytotoxic and antimicrobial activities",
volume = "143",
pages = "365-375",
doi = "10.1016/j.jsbmb.2014.06.005"
}

Krstić, N., Matić, I. Z., Juranić, Z., Novaković, I.,& Sladić, D.. (2014). Steroid dimers-In vitro cytotoxic and antimicrobial activities. in Journal of Steroid Biochemistry and Molecular Biology
Oxford : Pergamon-Elsevier Science Ltd., 143, 365-375.
https://doi.org/10.1016/j.jsbmb.2014.06.005

Krstić N, Matić IZ, Juranić Z, Novaković I, Sladić D. Steroid dimers-In vitro cytotoxic and antimicrobial activities. in Journal of Steroid Biochemistry and Molecular Biology. 2014;143:365-375.
doi:10.1016/j.jsbmb.2014.06.005 .

Krstić, Natalija, Matić, Ivana Z., Juranić, Zorica, Novaković, Irena, Sladić, Dušan, "Steroid dimers-In vitro cytotoxic and antimicrobial activities" in Journal of Steroid Biochemistry and Molecular Biology, 143 (2014):365-375,
https://doi.org/10.1016/j.jsbmb.2014.06.005 . .

TY  - JOUR
AU  - Milenković, Milica R.
AU  - Cantoni, Giulia
AU  - Bacchi, Alessia
AU  - Spasojević, Vojislav
AU  - Milenković, Marina
AU  - Sladić, Dušan
AU  - Krstić, Natalija
AU  - Anđelković, Katarina
PY  - 2014
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/1423
AB  - Complexes of Pd(II) and Fe(III) with the condensation derivative of 2-(diphenylphosphino)benzaldehyde and ethyl carbazate were synthesized, characterized, and their antimicrobial activity was evaluated. The structures of the Pd(II) and Fe(III) complexes in solid state were determined by IR, elemental analysis and X-ray analysis. The structure of Pd(II) complex in solution was determined by NMR spectroscopy. Results of magnetic measurements for Fe(III) complex were reported. In both complexes the ligand is coordinated as tridentate via the phosphorus, the imine nitrogen and the carbonyl oxygen atoms. Results of antimicrobial activity investigation indicate that the activity of the ligand is enhanced upon complexation, and that the MIC values of the iron complex to some bacterial strains are not much higher than those of cefotaxime.
PB  - Oxford : Pergamon-Elsevier Science Ltd
T2  - Polyhedron
T1  - Synthesis, characterization and antimicrobial activity of Pd(II) and Fe(III) complexes with ethyl (2E)-2-[2-(diphenylphosphino)benzylidene]hydrazinecarboxylate
VL  - 80
SP  - 47
EP  - 52
DO  - 10.1016/j.poly.2014.01.022
ER  - 

@article{
author = "Milenković, Milica R. and Cantoni, Giulia and Bacchi, Alessia and Spasojević, Vojislav and Milenković, Marina and Sladić, Dušan and Krstić, Natalija and Anđelković, Katarina",
year = "2014",
abstract = "Complexes of Pd(II) and Fe(III) with the condensation derivative of 2-(diphenylphosphino)benzaldehyde and ethyl carbazate were synthesized, characterized, and their antimicrobial activity was evaluated. The structures of the Pd(II) and Fe(III) complexes in solid state were determined by IR, elemental analysis and X-ray analysis. The structure of Pd(II) complex in solution was determined by NMR spectroscopy. Results of magnetic measurements for Fe(III) complex were reported. In both complexes the ligand is coordinated as tridentate via the phosphorus, the imine nitrogen and the carbonyl oxygen atoms. Results of antimicrobial activity investigation indicate that the activity of the ligand is enhanced upon complexation, and that the MIC values of the iron complex to some bacterial strains are not much higher than those of cefotaxime.",
publisher = "Oxford : Pergamon-Elsevier Science Ltd",
journal = "Polyhedron",
title = "Synthesis, characterization and antimicrobial activity of Pd(II) and Fe(III) complexes with ethyl (2E)-2-[2-(diphenylphosphino)benzylidene]hydrazinecarboxylate",
volume = "80",
pages = "47-52",
doi = "10.1016/j.poly.2014.01.022"
}

Milenković, M. R., Cantoni, G., Bacchi, A., Spasojević, V., Milenković, M., Sladić, D., Krstić, N.,& Anđelković, K.. (2014). Synthesis, characterization and antimicrobial activity of Pd(II) and Fe(III) complexes with ethyl (2E)-2-[2-(diphenylphosphino)benzylidene]hydrazinecarboxylate. in Polyhedron
Oxford : Pergamon-Elsevier Science Ltd., 80, 47-52.
https://doi.org/10.1016/j.poly.2014.01.022

Milenković MR, Cantoni G, Bacchi A, Spasojević V, Milenković M, Sladić D, Krstić N, Anđelković K. Synthesis, characterization and antimicrobial activity of Pd(II) and Fe(III) complexes with ethyl (2E)-2-[2-(diphenylphosphino)benzylidene]hydrazinecarboxylate. in Polyhedron. 2014;80:47-52.
doi:10.1016/j.poly.2014.01.022 .

Milenković, Milica R., Cantoni, Giulia, Bacchi, Alessia, Spasojević, Vojislav, Milenković, Marina, Sladić, Dušan, Krstić, Natalija, Anđelković, Katarina, "Synthesis, characterization and antimicrobial activity of Pd(II) and Fe(III) complexes with ethyl (2E)-2-[2-(diphenylphosphino)benzylidene]hydrazinecarboxylate" in Polyhedron, 80 (2014):47-52,
https://doi.org/10.1016/j.poly.2014.01.022 . .

TY  - JOUR
AU  - Krstić, Natalija
AU  - Pavlović, Vladimir D.
AU  - Novaković, Irena
AU  - Matić, Ivana Z.
AU  - Sladić, Dušan
PY  - 2013
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/1200
AB  - The reactions of 21-hydroxyprogesterone with Lawesson's reagent in toluene or gave four P-heterocyclic androst-4-ene derivatives (two tautomeric pairs): 4-(3-thioxoandrost-4-en-17-yl)-1,3,2-oxathiaphosphole-2- sulfide (2), 4-(3-thioxoandrost-4-en-17-ylidene)-1,3,2-oxathiaphospholane-2-sulfide (3), 4-(3-oxoandrost-4-en-17-yl)-1,3,2-oxathiaphosphole-2-sulfide (4), and 4-(3-oxoandrost-4-en-17-ylidene)-1,3,2- oxathiaphospholane-2-sulfide (5). The structures of all novel 17-substituted steroids were elucidated from their analytic and spectral data (HRMS, IR, 1D NMR and 2D NMR-HSQC, HMBC, NOESY, COSY). The detailed NMR analysis for all compounds revealed the presence of two pairs of signals in approx. 8:2 ratio indicating the existence of two diastereoisomers (a and b) with different configurations at the phosphorus atom. A parallel analysis of heteronuclear 2D - spectra (HSQC and HMBC) and homonuclear 2D spectra (NOESY and COSY) enabled complete and assignments of each isomer and provided evidence for the preferred configuration on phosphorus atom. Cytotoxic activity in vitro was tested against four tumor cell lines (human cervix carcinoma HeLa cells, chronic myelogenous leukemia K-562 and two human breast carcinoma MDA-MB-361 and MDA-MB-453 cells). Compounds 3a,b and 4a,b showed a poor activity against HeLa and MDA-MB-453 cell lines, while against MDA-MB-361 cell line, all tested compounds exerted very weak cytotoxic effect. All compounds exerted moderate activity against K562 cells. Antimicrobial activity against Gram-positive, Gram-negative bacteria and fungal cells, and toxicity to brine shrimp Artemia salina were evaluated. All tested compounds showed strong antifungal activity.
PB  - Springer, Dordrecht
T2  - Molecular Diversity
T1  - Synthesis, characterization and biological evaluation of some novel P-heterocyclic androst-4-ene derivatives
VL  - 17
IS  - 3
SP  - 547
EP  - 561
DO  - 10.1007/s11030-013-9455-9
ER  - 

@article{
author = "Krstić, Natalija and Pavlović, Vladimir D. and Novaković, Irena and Matić, Ivana Z. and Sladić, Dušan",
year = "2013",
abstract = "The reactions of 21-hydroxyprogesterone with Lawesson's reagent in toluene or gave four P-heterocyclic androst-4-ene derivatives (two tautomeric pairs): 4-(3-thioxoandrost-4-en-17-yl)-1,3,2-oxathiaphosphole-2- sulfide (2), 4-(3-thioxoandrost-4-en-17-ylidene)-1,3,2-oxathiaphospholane-2-sulfide (3), 4-(3-oxoandrost-4-en-17-yl)-1,3,2-oxathiaphosphole-2-sulfide (4), and 4-(3-oxoandrost-4-en-17-ylidene)-1,3,2- oxathiaphospholane-2-sulfide (5). The structures of all novel 17-substituted steroids were elucidated from their analytic and spectral data (HRMS, IR, 1D NMR and 2D NMR-HSQC, HMBC, NOESY, COSY). The detailed NMR analysis for all compounds revealed the presence of two pairs of signals in approx. 8:2 ratio indicating the existence of two diastereoisomers (a and b) with different configurations at the phosphorus atom. A parallel analysis of heteronuclear 2D - spectra (HSQC and HMBC) and homonuclear 2D spectra (NOESY and COSY) enabled complete and assignments of each isomer and provided evidence for the preferred configuration on phosphorus atom. Cytotoxic activity in vitro was tested against four tumor cell lines (human cervix carcinoma HeLa cells, chronic myelogenous leukemia K-562 and two human breast carcinoma MDA-MB-361 and MDA-MB-453 cells). Compounds 3a,b and 4a,b showed a poor activity against HeLa and MDA-MB-453 cell lines, while against MDA-MB-361 cell line, all tested compounds exerted very weak cytotoxic effect. All compounds exerted moderate activity against K562 cells. Antimicrobial activity against Gram-positive, Gram-negative bacteria and fungal cells, and toxicity to brine shrimp Artemia salina were evaluated. All tested compounds showed strong antifungal activity.",
publisher = "Springer, Dordrecht",
journal = "Molecular Diversity",
title = "Synthesis, characterization and biological evaluation of some novel P-heterocyclic androst-4-ene derivatives",
volume = "17",
number = "3",
pages = "547-561",
doi = "10.1007/s11030-013-9455-9"
}

Krstić, N., Pavlović, V. D., Novaković, I., Matić, I. Z.,& Sladić, D.. (2013). Synthesis, characterization and biological evaluation of some novel P-heterocyclic androst-4-ene derivatives. in Molecular Diversity
Springer, Dordrecht., 17(3), 547-561.
https://doi.org/10.1007/s11030-013-9455-9

Krstić N, Pavlović VD, Novaković I, Matić IZ, Sladić D. Synthesis, characterization and biological evaluation of some novel P-heterocyclic androst-4-ene derivatives. in Molecular Diversity. 2013;17(3):547-561.
doi:10.1007/s11030-013-9455-9 .

Krstić, Natalija, Pavlović, Vladimir D., Novaković, Irena, Matić, Ivana Z., Sladić, Dušan, "Synthesis, characterization and biological evaluation of some novel P-heterocyclic androst-4-ene derivatives" in Molecular Diversity, 17, no. 3 (2013):547-561,
https://doi.org/10.1007/s11030-013-9455-9 . .

TY  - JOUR
AU  - Krstić, Natalija
AU  - Bjelaković, Mira
AU  - Pavlović, Vladimir D.
AU  - Robeyns, Koen
AU  - Juranić, Zorica
AU  - Matić, Ivana Z.
AU  - Novaković, Irena
AU  - Sladić, Dušan
PY  - 2012
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/945
AB  - The reactions of 17 alpha-hydroxyprogesterone with Lawesson's reagent (LR) in toluene, CH2Cl2 and/or CCl4 gave, depending on the duration of the reaction, two diastereoisomeric androst-4-en-17-spiro-1,3,2-oxathiaphospholane-2-sulfide pairs 2a,b and 3a,b in approximately 7:3 ratio, differing in configuration at the phosphorus atom. A parallel analysis of heteronuclear 2D H-1-C-13 spectra (HSQC and HMBC) and homo-nuclear 2D spectra (NOESY) enabled complete H-1 and C-13 assignments of each isomer. Also, analysis of NOESY correlations provided evidence for the preferred conformation. X-ray analysis of 3a confirmed the structure and absolute configuration on phosphorus. A pathway for the formation of 1,3,2-oxathiaphospholane ring was proposed. Cytotoxic activity in vitro was tested against three tumor cell lines (human cervix carcinoma HeLa cells and two human breast carcinoma MDA-MB-361 and MDA-MB-453 cells). Compound 3a and mixture 3a,b showed a moderate activity against HeLa and MDA-MB-453 cell lines while against MDA-MB-361 cell line all tested compounds exerted very weak cytotoxic effect. Antimicrobial activity against Gram-positive, Gram-negative bacteria and fungal cells, toxicity to brine shrimp Artemia sauna, were evaluated. All tested compounds showed strong antifungal activity.
PB  - Elsevier Science Inc, New York
T2  - Steroids
T1  - New androst-4-en-17-spiro-1,3,2-oxathiaphospholanes. Synthesis, assignment of absolute configuration and in vitro cytotoxic and antimicrobial activities
VL  - 77
IS  - 5
SP  - 558
EP  - 565
DO  - 10.1016/j.steroids.2012.01.021
ER  - 

@article{
author = "Krstić, Natalija and Bjelaković, Mira and Pavlović, Vladimir D. and Robeyns, Koen and Juranić, Zorica and Matić, Ivana Z. and Novaković, Irena and Sladić, Dušan",
year = "2012",
abstract = "The reactions of 17 alpha-hydroxyprogesterone with Lawesson's reagent (LR) in toluene, CH2Cl2 and/or CCl4 gave, depending on the duration of the reaction, two diastereoisomeric androst-4-en-17-spiro-1,3,2-oxathiaphospholane-2-sulfide pairs 2a,b and 3a,b in approximately 7:3 ratio, differing in configuration at the phosphorus atom. A parallel analysis of heteronuclear 2D H-1-C-13 spectra (HSQC and HMBC) and homo-nuclear 2D spectra (NOESY) enabled complete H-1 and C-13 assignments of each isomer. Also, analysis of NOESY correlations provided evidence for the preferred conformation. X-ray analysis of 3a confirmed the structure and absolute configuration on phosphorus. A pathway for the formation of 1,3,2-oxathiaphospholane ring was proposed. Cytotoxic activity in vitro was tested against three tumor cell lines (human cervix carcinoma HeLa cells and two human breast carcinoma MDA-MB-361 and MDA-MB-453 cells). Compound 3a and mixture 3a,b showed a moderate activity against HeLa and MDA-MB-453 cell lines while against MDA-MB-361 cell line all tested compounds exerted very weak cytotoxic effect. Antimicrobial activity against Gram-positive, Gram-negative bacteria and fungal cells, toxicity to brine shrimp Artemia sauna, were evaluated. All tested compounds showed strong antifungal activity.",
publisher = "Elsevier Science Inc, New York",
journal = "Steroids",
title = "New androst-4-en-17-spiro-1,3,2-oxathiaphospholanes. Synthesis, assignment of absolute configuration and in vitro cytotoxic and antimicrobial activities",
volume = "77",
number = "5",
pages = "558-565",
doi = "10.1016/j.steroids.2012.01.021"
}

Krstić, N., Bjelaković, M., Pavlović, V. D., Robeyns, K., Juranić, Z., Matić, I. Z., Novaković, I.,& Sladić, D.. (2012). New androst-4-en-17-spiro-1,3,2-oxathiaphospholanes. Synthesis, assignment of absolute configuration and in vitro cytotoxic and antimicrobial activities. in Steroids
Elsevier Science Inc, New York., 77(5), 558-565.
https://doi.org/10.1016/j.steroids.2012.01.021

Krstić N, Bjelaković M, Pavlović VD, Robeyns K, Juranić Z, Matić IZ, Novaković I, Sladić D. New androst-4-en-17-spiro-1,3,2-oxathiaphospholanes. Synthesis, assignment of absolute configuration and in vitro cytotoxic and antimicrobial activities. in Steroids. 2012;77(5):558-565.
doi:10.1016/j.steroids.2012.01.021 .

Krstić, Natalija, Bjelaković, Mira, Pavlović, Vladimir D., Robeyns, Koen, Juranić, Zorica, Matić, Ivana Z., Novaković, Irena, Sladić, Dušan, "New androst-4-en-17-spiro-1,3,2-oxathiaphospholanes. Synthesis, assignment of absolute configuration and in vitro cytotoxic and antimicrobial activities" in Steroids, 77, no. 5 (2012):558-565,
https://doi.org/10.1016/j.steroids.2012.01.021 . .

TY  - JOUR
AU  - Bjelaković, Mira
AU  - Krstić, Natalija
AU  - Milić, Dragana
AU  - Kop, Tatjana
AU  - Robeyns, Koen
AU  - Pavlović, Vladimir D.
PY  - 2012
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/1114
AB  - The present study is concerned with the oxidative behaviour of unsaturated and epoxy 5-oxo-5,10-secosteroids in the presence of m-CPBA or TFAA-UHP as oxidants in order to investigate potential parameters controlling the chemoselectivity and regioselectivity. In the study we discovered a striking difference in the chemical behaviour of stereoisomeric compounds, (Z)- and (E)-3 beta-acetoxy-5,10-secocholest-1(10)-en-5-ones, as well as 1S,10R- and 1R,10R-epoxides. The secoketones were oxidized with exclusively C-6 migration and Baeyer-Villiger rearrangement product formation, whereas their stereoisomers provided the ring-contracted products, without lactone formation. The preferred conformation of expanded and contracted rings was established by NOESY correlations. The structures of two obtained lactones were also confirmed by X-ray analysis. The mechanistic and stereochemical aspects of these transformations are discussed.
PB  - Oxford : Pergamon-Elsevier Science Ltd
T2  - Tetrahedron
T1  - Oxidative 10-membered ring expansion and contraction of stereoisomeric 1(10)-unsaturated and 1,10-epoxy-5-oxo-5,10-secosteroids induced by peracids
VL  - 68
IS  - 36
SP  - 7479
EP  - 7488
DO  - 10.1016/j.tet.2012.06.024
ER  - 

@article{
author = "Bjelaković, Mira and Krstić, Natalija and Milić, Dragana and Kop, Tatjana and Robeyns, Koen and Pavlović, Vladimir D.",
year = "2012",
abstract = "The present study is concerned with the oxidative behaviour of unsaturated and epoxy 5-oxo-5,10-secosteroids in the presence of m-CPBA or TFAA-UHP as oxidants in order to investigate potential parameters controlling the chemoselectivity and regioselectivity. In the study we discovered a striking difference in the chemical behaviour of stereoisomeric compounds, (Z)- and (E)-3 beta-acetoxy-5,10-secocholest-1(10)-en-5-ones, as well as 1S,10R- and 1R,10R-epoxides. The secoketones were oxidized with exclusively C-6 migration and Baeyer-Villiger rearrangement product formation, whereas their stereoisomers provided the ring-contracted products, without lactone formation. The preferred conformation of expanded and contracted rings was established by NOESY correlations. The structures of two obtained lactones were also confirmed by X-ray analysis. The mechanistic and stereochemical aspects of these transformations are discussed.",
publisher = "Oxford : Pergamon-Elsevier Science Ltd",
journal = "Tetrahedron",
title = "Oxidative 10-membered ring expansion and contraction of stereoisomeric 1(10)-unsaturated and 1,10-epoxy-5-oxo-5,10-secosteroids induced by peracids",
volume = "68",
number = "36",
pages = "7479-7488",
doi = "10.1016/j.tet.2012.06.024"
}

Bjelaković, M., Krstić, N., Milić, D., Kop, T., Robeyns, K.,& Pavlović, V. D.. (2012). Oxidative 10-membered ring expansion and contraction of stereoisomeric 1(10)-unsaturated and 1,10-epoxy-5-oxo-5,10-secosteroids induced by peracids. in Tetrahedron
Oxford : Pergamon-Elsevier Science Ltd., 68(36), 7479-7488.
https://doi.org/10.1016/j.tet.2012.06.024

Bjelaković M, Krstić N, Milić D, Kop T, Robeyns K, Pavlović VD. Oxidative 10-membered ring expansion and contraction of stereoisomeric 1(10)-unsaturated and 1,10-epoxy-5-oxo-5,10-secosteroids induced by peracids. in Tetrahedron. 2012;68(36):7479-7488.
doi:10.1016/j.tet.2012.06.024 .

Bjelaković, Mira, Krstić, Natalija, Milić, Dragana, Kop, Tatjana, Robeyns, Koen, Pavlović, Vladimir D., "Oxidative 10-membered ring expansion and contraction of stereoisomeric 1(10)-unsaturated and 1,10-epoxy-5-oxo-5,10-secosteroids induced by peracids" in Tetrahedron, 68, no. 36 (2012):7479-7488,
https://doi.org/10.1016/j.tet.2012.06.024 . .

TY  - JOUR
AU  - Krstić, Natalija
AU  - Bjelaković, Mira
AU  - Dabović, Milan
AU  - Pavlović, Vladimir D.
PY  - 2010
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/629
AB  - The reactions of selected alpha,beta-unsaturated steroidal ketones with Lawesson's reagent (LR) in CH(2)Cl(2) and toluene under the standard reaction conditions and with a combination of phosphorus pentasulfide with hexamethyldisiloxane (P(4)S(10)/HMDO) in 1,2-dichlorobenzene (ODCB) under microwave irradiation were investigated and for this purpose several cholestane, androstane and pregnane carbonyl derivatives were chosen. Depending on the reagent and the solvent, 19 new sulfur containing compounds, including dithiones 4c and 4d, alpha,beta-unsaturated 3-thiones 3a-e, dimer-sulfides 2a-e, 1,2,4-trithiolanes 5a-e and phosphonotrithioates 6b-e were synthesized. All newly prepared compounds were characterized by IR, (1)H- and (13)C-NMR spectroscopy and elemental analysis.
PB  - MDPI
T2  - Molecules
T1  - Thionation of Some alpha,beta-Unsaturated Steroidal Ketones
VL  - 15
IS  - 5
SP  - 3462
EP  - 3477
DO  - 10.3390/molecules15053462
ER  - 

@article{
author = "Krstić, Natalija and Bjelaković, Mira and Dabović, Milan and Pavlović, Vladimir D.",
year = "2010",
abstract = "The reactions of selected alpha,beta-unsaturated steroidal ketones with Lawesson's reagent (LR) in CH(2)Cl(2) and toluene under the standard reaction conditions and with a combination of phosphorus pentasulfide with hexamethyldisiloxane (P(4)S(10)/HMDO) in 1,2-dichlorobenzene (ODCB) under microwave irradiation were investigated and for this purpose several cholestane, androstane and pregnane carbonyl derivatives were chosen. Depending on the reagent and the solvent, 19 new sulfur containing compounds, including dithiones 4c and 4d, alpha,beta-unsaturated 3-thiones 3a-e, dimer-sulfides 2a-e, 1,2,4-trithiolanes 5a-e and phosphonotrithioates 6b-e were synthesized. All newly prepared compounds were characterized by IR, (1)H- and (13)C-NMR spectroscopy and elemental analysis.",
publisher = "MDPI",
journal = "Molecules",
title = "Thionation of Some alpha,beta-Unsaturated Steroidal Ketones",
volume = "15",
number = "5",
pages = "3462-3477",
doi = "10.3390/molecules15053462"
}

Krstić, N., Bjelaković, M., Dabović, M.,& Pavlović, V. D.. (2010). Thionation of Some alpha,beta-Unsaturated Steroidal Ketones. in Molecules
MDPI., 15(5), 3462-3477.
https://doi.org/10.3390/molecules15053462

Krstić N, Bjelaković M, Dabović M, Pavlović VD. Thionation of Some alpha,beta-Unsaturated Steroidal Ketones. in Molecules. 2010;15(5):3462-3477.
doi:10.3390/molecules15053462 .

Krstić, Natalija, Bjelaković, Mira, Dabović, Milan, Pavlović, Vladimir D., "Thionation of Some alpha,beta-Unsaturated Steroidal Ketones" in Molecules, 15, no. 5 (2010):3462-3477,
https://doi.org/10.3390/molecules15053462 . .

TY  - JOUR
AU  - Bjelaković, Mira
AU  - Krstić, Natalija
AU  - Todorović, Nina
AU  - Krunić, Aleksej
AU  - Tinant, Bernard
AU  - Dabović, Milan
AU  - Pavlović, Vladimir D.
PY  - 2009
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/620
AB  - In this paper a synthetic pathway to the modified 5,10:13,14-bisfragmentation cholestane derivatives 8-14 is described. The synthesis involves introduction of the 5α- and 14α-hydroxyl groups in the cholestane molecule and subsequent cleavage of the C(5)-C(10) bond in 5α,14α-dihydroxycholestan-3β-yl acetate (4) with the HgO/I2 reagent and the C(13)-C(14) bond in the stereoisomeric 14α-hydroxy-5,10-secosteroids 5 and 6 with the Pb(OAc)4/I2 reagent. Complete and unambiguous 1H and 13C NMR resonance assignments of the obtained secosteroids, as well as the solution conformations of their 10- and 9-membered rings were determined by extensive analysis of 1D and 2D NMR spectral data. The structures and the solid-state conformations of 5,10-secosteroids 5-7 were confirmed by X-ray analysis. All diseco-compounds have a novel 5,10:13,14-disecocholestane skeleton.
PB  - Oxford : Pergamon-Elsevier Science Ltd
T2  - Tetrahedron
T1  - 5,10:13,14-Disecosteroids: novel modified steroids containing 10- and 9-membered rings
VL  - 65
IS  - 46
SP  - 9557
EP  - 9568
DO  - 10.1016/j.tet.2009.09.066
ER  - 

@article{
author = "Bjelaković, Mira and Krstić, Natalija and Todorović, Nina and Krunić, Aleksej and Tinant, Bernard and Dabović, Milan and Pavlović, Vladimir D.",
year = "2009",
abstract = "In this paper a synthetic pathway to the modified 5,10:13,14-bisfragmentation cholestane derivatives 8-14 is described. The synthesis involves introduction of the 5α- and 14α-hydroxyl groups in the cholestane molecule and subsequent cleavage of the C(5)-C(10) bond in 5α,14α-dihydroxycholestan-3β-yl acetate (4) with the HgO/I2 reagent and the C(13)-C(14) bond in the stereoisomeric 14α-hydroxy-5,10-secosteroids 5 and 6 with the Pb(OAc)4/I2 reagent. Complete and unambiguous 1H and 13C NMR resonance assignments of the obtained secosteroids, as well as the solution conformations of their 10- and 9-membered rings were determined by extensive analysis of 1D and 2D NMR spectral data. The structures and the solid-state conformations of 5,10-secosteroids 5-7 were confirmed by X-ray analysis. All diseco-compounds have a novel 5,10:13,14-disecocholestane skeleton.",
publisher = "Oxford : Pergamon-Elsevier Science Ltd",
journal = "Tetrahedron",
title = "5,10:13,14-Disecosteroids: novel modified steroids containing 10- and 9-membered rings",
volume = "65",
number = "46",
pages = "9557-9568",
doi = "10.1016/j.tet.2009.09.066"
}

Bjelaković, M., Krstić, N., Todorović, N., Krunić, A., Tinant, B., Dabović, M.,& Pavlović, V. D.. (2009). 5,10:13,14-Disecosteroids: novel modified steroids containing 10- and 9-membered rings. in Tetrahedron
Oxford : Pergamon-Elsevier Science Ltd., 65(46), 9557-9568.
https://doi.org/10.1016/j.tet.2009.09.066

Bjelaković M, Krstić N, Todorović N, Krunić A, Tinant B, Dabović M, Pavlović VD. 5,10:13,14-Disecosteroids: novel modified steroids containing 10- and 9-membered rings. in Tetrahedron. 2009;65(46):9557-9568.
doi:10.1016/j.tet.2009.09.066 .

Bjelaković, Mira, Krstić, Natalija, Todorović, Nina, Krunić, Aleksej, Tinant, Bernard, Dabović, Milan, Pavlović, Vladimir D., "5,10:13,14-Disecosteroids: novel modified steroids containing 10- and 9-membered rings" in Tetrahedron, 65, no. 46 (2009):9557-9568,
https://doi.org/10.1016/j.tet.2009.09.066 . .

TY  - JOUR
AU  - Krstić, Natalija
AU  - Bjelaković, Mira
AU  - Žižak, Željko
AU  - Pavlović, Mirjana
AU  - Juranić, Zorica
AU  - Pavlović, Vladimir D.
PY  - 2007
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/363
AB  - The antiproliferative activity of previously synthesized (Z)-cholest-4-en-6-one oxime (1), (E)-cholest-4-en-6-one oxime (2), 7-aza-B-homocholest-4-en-6-one (3) and 6-aza-B-homocholest-4-en-7-one (4) and newly synthesized 6-thioxo-7-aza-B-homocholest-4-ene (5) and 6-aza-7-thioxo-B-homocholest-4-ene (6) was tested for their possible effects against two human tumor cell lines, cervical carcinoma (HeLa) and chronic myelogenous leukemia (K-562). Compounds 1-6, exerted a dose-dependent antiproliferative effect toward cell lines used in experimental design, showing high selectivity in their action for tumor cells in comparison to normal immunocompetent cells (non-stimulated PBMC and PHA-stimulated PBMC). Compounds 2, 3 and 4 exhibited a very high but selective antitumor activity, by inducing apoptosis in sensitive, for that purpose targeted tumor cell line (HeLa cells). Low toxic effect upon both non-stimulated, and PHA stimulated PBMCs from control, healthy volunteers, has been detected for compounds 1, 2, 3 and 4. The possible reasons for profound differences in the effects of this spectrum of steroidal compounds between tumor cell lines and normal stimulated and non-stimulated PBMCs are discussed. The molecular mechanisms for apoptotic events in HeLa cell line are suggested. The guidelines for further research are underlined.
PB  - Elsevier
T2  - Steroids
T1  - Synthesis of some steroidal oximes, lactams, thiolactams and their antitumor activities
VL  - 72
IS  - 5
SP  - 406
EP  - 414
DO  - 10.1016/j.steroids.2007.02.005
ER  - 

@article{
author = "Krstić, Natalija and Bjelaković, Mira and Žižak, Željko and Pavlović, Mirjana and Juranić, Zorica and Pavlović, Vladimir D.",
year = "2007",
abstract = "The antiproliferative activity of previously synthesized (Z)-cholest-4-en-6-one oxime (1), (E)-cholest-4-en-6-one oxime (2), 7-aza-B-homocholest-4-en-6-one (3) and 6-aza-B-homocholest-4-en-7-one (4) and newly synthesized 6-thioxo-7-aza-B-homocholest-4-ene (5) and 6-aza-7-thioxo-B-homocholest-4-ene (6) was tested for their possible effects against two human tumor cell lines, cervical carcinoma (HeLa) and chronic myelogenous leukemia (K-562). Compounds 1-6, exerted a dose-dependent antiproliferative effect toward cell lines used in experimental design, showing high selectivity in their action for tumor cells in comparison to normal immunocompetent cells (non-stimulated PBMC and PHA-stimulated PBMC). Compounds 2, 3 and 4 exhibited a very high but selective antitumor activity, by inducing apoptosis in sensitive, for that purpose targeted tumor cell line (HeLa cells). Low toxic effect upon both non-stimulated, and PHA stimulated PBMCs from control, healthy volunteers, has been detected for compounds 1, 2, 3 and 4. The possible reasons for profound differences in the effects of this spectrum of steroidal compounds between tumor cell lines and normal stimulated and non-stimulated PBMCs are discussed. The molecular mechanisms for apoptotic events in HeLa cell line are suggested. The guidelines for further research are underlined.",
publisher = "Elsevier",
journal = "Steroids",
title = "Synthesis of some steroidal oximes, lactams, thiolactams and their antitumor activities",
volume = "72",
number = "5",
pages = "406-414",
doi = "10.1016/j.steroids.2007.02.005"
}

Krstić, N., Bjelaković, M., Žižak, Ž., Pavlović, M., Juranić, Z.,& Pavlović, V. D.. (2007). Synthesis of some steroidal oximes, lactams, thiolactams and their antitumor activities. in Steroids
Elsevier., 72(5), 406-414.
https://doi.org/10.1016/j.steroids.2007.02.005

Krstić N, Bjelaković M, Žižak Ž, Pavlović M, Juranić Z, Pavlović VD. Synthesis of some steroidal oximes, lactams, thiolactams and their antitumor activities. in Steroids. 2007;72(5):406-414.
doi:10.1016/j.steroids.2007.02.005 .

Krstić, Natalija, Bjelaković, Mira, Žižak, Željko, Pavlović, Mirjana, Juranić, Zorica, Pavlović, Vladimir D., "Synthesis of some steroidal oximes, lactams, thiolactams and their antitumor activities" in Steroids, 72, no. 5 (2007):406-414,
https://doi.org/10.1016/j.steroids.2007.02.005 . .

TY  - JOUR
AU  - Bjelaković, Mira
AU  - Krstić, Natalija
AU  - Juranić, Nenad
AU  - Dabović, Milan
AU  - Gojković, S.V.
AU  - Kessler, M.
AU  - Kalvoda, J.
AU  - Pavlović, Vladimir D.
PY  - 2007
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/358
AB  - We report herein the synthesis of a novel modified steroid with two rigidly positioned amino acids in C- and N-protected forms (Gly-OtBu and N-Fmoc-l-Phe) at the angular positions (C-18 methylamino group and C-19 carboxylic function) of the steroid nucleus via amide bonds, starting from 18-cyanopregnenolone acetate over 10 steps. In an attempt to gain more insight into the structural and conformational features of this novel 18-Phe,19-Gly-containing steroidal compound, we describe the detailed 2D NMR spectral analysis. Despite the large size and the conformational flexibility of the amino acid units in this molecule, conformational analysis by NOESY connectivities showed the existence of mainly one conformation (∼95%) in CDCl3 solution with approximately parallel orientation of the phenylalanine and glycine moieties.
PB  - Oxford : Pergamon-Elsevier Science Ltd
T2  - Tetrahedron
T1  - Steroid template associated peptides: design, synthesis and 2D NMR characterization of a novel protected 18-Phe,19-Gly-containing steroidal compound
VL  - 63
IS  - 40
SP  - 9960
EP  - 9969
DO  - 10.1016/j.tet.2007.07.056
ER  - 

@article{
author = "Bjelaković, Mira and Krstić, Natalija and Juranić, Nenad and Dabović, Milan and Gojković, S.V. and Kessler, M. and Kalvoda, J. and Pavlović, Vladimir D.",
year = "2007",
abstract = "We report herein the synthesis of a novel modified steroid with two rigidly positioned amino acids in C- and N-protected forms (Gly-OtBu and N-Fmoc-l-Phe) at the angular positions (C-18 methylamino group and C-19 carboxylic function) of the steroid nucleus via amide bonds, starting from 18-cyanopregnenolone acetate over 10 steps. In an attempt to gain more insight into the structural and conformational features of this novel 18-Phe,19-Gly-containing steroidal compound, we describe the detailed 2D NMR spectral analysis. Despite the large size and the conformational flexibility of the amino acid units in this molecule, conformational analysis by NOESY connectivities showed the existence of mainly one conformation (∼95%) in CDCl3 solution with approximately parallel orientation of the phenylalanine and glycine moieties.",
publisher = "Oxford : Pergamon-Elsevier Science Ltd",
journal = "Tetrahedron",
title = "Steroid template associated peptides: design, synthesis and 2D NMR characterization of a novel protected 18-Phe,19-Gly-containing steroidal compound",
volume = "63",
number = "40",
pages = "9960-9969",
doi = "10.1016/j.tet.2007.07.056"
}

Bjelaković, M., Krstić, N., Juranić, N., Dabović, M., Gojković, S.V., Kessler, M., Kalvoda, J.,& Pavlović, V. D.. (2007). Steroid template associated peptides: design, synthesis and 2D NMR characterization of a novel protected 18-Phe,19-Gly-containing steroidal compound. in Tetrahedron
Oxford : Pergamon-Elsevier Science Ltd., 63(40), 9960-9969.
https://doi.org/10.1016/j.tet.2007.07.056

Bjelaković M, Krstić N, Juranić N, Dabović M, Gojković S, Kessler M, Kalvoda J, Pavlović VD. Steroid template associated peptides: design, synthesis and 2D NMR characterization of a novel protected 18-Phe,19-Gly-containing steroidal compound. in Tetrahedron. 2007;63(40):9960-9969.
doi:10.1016/j.tet.2007.07.056 .

Bjelaković, Mira, Krstić, Natalija, Juranić, Nenad, Dabović, Milan, Gojković, S.V., Kessler, M., Kalvoda, J., Pavlović, Vladimir D., "Steroid template associated peptides: design, synthesis and 2D NMR characterization of a novel protected 18-Phe,19-Gly-containing steroidal compound" in Tetrahedron, 63, no. 40 (2007):9960-9969,
https://doi.org/10.1016/j.tet.2007.07.056 . .

TY  - JOUR
AU  - Bjelaković, Mira
AU  - Krstić, Natalija
AU  - Tinant, Bernard
AU  - Kalvoda, Jaroslav
AU  - Csanadi, Janos
AU  - Pavlović, Vladimir D.
PY  - 2005
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/4186
AB  - The conformations of (Z)‐ and (E)‐5‐oxo‐B‐nor‐5,10‐secocholest‐1(10)‐en‐3β‐yl acetates (2 and 3, resp.) were examined by a combination of X‐ray crystallographic analysis and NMR spectroscopy, with emphasis on the geometry of the cyclononenone moiety. The 1H‐ and 13C‐NMR spectra showed that the unsaturated nine‐membered ring of (E)‐isomer 3 in C6D6 and (D6)acetone solution exists in a sole conformation of type B1, which is similar to its solid‐state conformation. The (Z)‐isomer 2 in C6D6, CDCl3, and (D6)acetone solution, however, exists in two conformational forms of different families, with different orientation of the carbonyl group, the predominant form (85%) corresponding to the conformation of type A1 and the minor (15%) to the conformation A2 present also in the crystalline state. In this solid‐state conformations of the nine‐membered ring of both compounds, the 19‐Me and 5‐oxo groups are ‘β’‐oriented. The NMR analysis suggests that the nine‐membered ring of 4 has a conformation of type C1 in CDCl3 solution.
PB  - Wiley
T2  - Helvetica Chimica Acta
T1  - Conformations of the Nine-Membered Ring in the B-Nor-5,10-secosteroids. X-Ray and NMR Analysis
VL  - 88
IS  - 10
SP  - 2812
EP  - 2821
DO  - 10.1002/hlca.200590221
ER  - 

@article{
author = "Bjelaković, Mira and Krstić, Natalija and Tinant, Bernard and Kalvoda, Jaroslav and Csanadi, Janos and Pavlović, Vladimir D.",
year = "2005",
abstract = "The conformations of (Z)‐ and (E)‐5‐oxo‐B‐nor‐5,10‐secocholest‐1(10)‐en‐3β‐yl acetates (2 and 3, resp.) were examined by a combination of X‐ray crystallographic analysis and NMR spectroscopy, with emphasis on the geometry of the cyclononenone moiety. The 1H‐ and 13C‐NMR spectra showed that the unsaturated nine‐membered ring of (E)‐isomer 3 in C6D6 and (D6)acetone solution exists in a sole conformation of type B1, which is similar to its solid‐state conformation. The (Z)‐isomer 2 in C6D6, CDCl3, and (D6)acetone solution, however, exists in two conformational forms of different families, with different orientation of the carbonyl group, the predominant form (85%) corresponding to the conformation of type A1 and the minor (15%) to the conformation A2 present also in the crystalline state. In this solid‐state conformations of the nine‐membered ring of both compounds, the 19‐Me and 5‐oxo groups are ‘β’‐oriented. The NMR analysis suggests that the nine‐membered ring of 4 has a conformation of type C1 in CDCl3 solution.",
publisher = "Wiley",
journal = "Helvetica Chimica Acta",
title = "Conformations of the Nine-Membered Ring in the B-Nor-5,10-secosteroids. X-Ray and NMR Analysis",
volume = "88",
number = "10",
pages = "2812-2821",
doi = "10.1002/hlca.200590221"
}

Bjelaković, M., Krstić, N., Tinant, B., Kalvoda, J., Csanadi, J.,& Pavlović, Vladimir D.. (2005). Conformations of the Nine-Membered Ring in the B-Nor-5,10-secosteroids. X-Ray and NMR Analysis. in Helvetica Chimica Acta
Wiley., 88(10), 2812-2821.
https://doi.org/10.1002/hlca.200590221

Bjelaković M, Krstić N, Tinant B, Kalvoda J, Csanadi J, Pavlović V. Conformations of the Nine-Membered Ring in the B-Nor-5,10-secosteroids. X-Ray and NMR Analysis. in Helvetica Chimica Acta. 2005;88(10):2812-2821.
doi:10.1002/hlca.200590221 .

Bjelaković, Mira, Krstić, Natalija, Tinant, Bernard, Kalvoda, Jaroslav, Csanadi, Janos, Pavlović, Vladimir D., "Conformations of the Nine-Membered Ring in the B-Nor-5,10-secosteroids. X-Ray and NMR Analysis" in Helvetica Chimica Acta, 88, no. 10 (2005):2812-2821,
https://doi.org/10.1002/hlca.200590221 . .

TY  - JOUR
AU  - Krstić, Natalija
AU  - Bjelaković, Mira
AU  - Dabović, Milan
AU  - Lorenc, Ljubinka
AU  - Pavlović, Vladimir D.
PY  - 2004
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/148
AB  - Beckmann rearrangement of (Z)-cholest-4-en-6-one oxime (4) (prepared in 4 steps starting from cholest-5-en-3β-ol ο1)) with thionyl chloride in dioxane solution afforded an enamide-type lactam, i.e. 7-aza-B-homocholest-4-en-6-one (6) as a single product. Photoreaction of the same compound in methanol or benzene-acetic acid solution gave a mixture of products, with the formation of the parent ketone 3 and the occurrence of Z/E isomerization, while the lactam 6 was obtained only when the reaction was performed in methanol and then in very low yield (7%).
AB  - Bekmanovo premeštanje (Z)-holest-4-en-6-on oksima (4) (koji je dobijen u 4 faze, polazeći od holest-5-en-3 β-ola (1)) sa tionil-hloridom u dioksanskom rastvoru, kao jedini proizvod daje laktam enamidnog tipa, tj. 7-aza-B-homoholest-4-en-6-on (6). Fotoreakcijom istog jedinjenja u metanolu ili u rastvoru benzen-sirćetna kiselina, nastaje smesa proizvoda koju čine polazni keton 3 i proizvodi Z/E izomerizacije, dok je laktam 6 dobiven u vrlo niskom prinosu (7%) samo u metanolnom rastvoru.
PB  - Serbian Chemical Society
T2  - Journal of the Serbian Chemical Society
T1  - Photochemical and Beckmann rearrangement of (Z)-cholest-4-en-6-one oxime
T1  - Fotohemijsko i Bekmanovo premeštanje(z)-holest-4-en-6-on oksima
VL  - 69
IS  - 6
SP  - 413
EP  - 420
DO  - 10.2298/JSC0406413K
ER  - 

@article{
author = "Krstić, Natalija and Bjelaković, Mira and Dabović, Milan and Lorenc, Ljubinka and Pavlović, Vladimir D.",
year = "2004",
abstract = "Beckmann rearrangement of (Z)-cholest-4-en-6-one oxime (4) (prepared in 4 steps starting from cholest-5-en-3β-ol ο1)) with thionyl chloride in dioxane solution afforded an enamide-type lactam, i.e. 7-aza-B-homocholest-4-en-6-one (6) as a single product. Photoreaction of the same compound in methanol or benzene-acetic acid solution gave a mixture of products, with the formation of the parent ketone 3 and the occurrence of Z/E isomerization, while the lactam 6 was obtained only when the reaction was performed in methanol and then in very low yield (7%)., Bekmanovo premeštanje (Z)-holest-4-en-6-on oksima (4) (koji je dobijen u 4 faze, polazeći od holest-5-en-3 β-ola (1)) sa tionil-hloridom u dioksanskom rastvoru, kao jedini proizvod daje laktam enamidnog tipa, tj. 7-aza-B-homoholest-4-en-6-on (6). Fotoreakcijom istog jedinjenja u metanolu ili u rastvoru benzen-sirćetna kiselina, nastaje smesa proizvoda koju čine polazni keton 3 i proizvodi Z/E izomerizacije, dok je laktam 6 dobiven u vrlo niskom prinosu (7%) samo u metanolnom rastvoru.",
publisher = "Serbian Chemical Society",
journal = "Journal of the Serbian Chemical Society",
title = "Photochemical and Beckmann rearrangement of (Z)-cholest-4-en-6-one oxime, Fotohemijsko i Bekmanovo premeštanje(z)-holest-4-en-6-on oksima",
volume = "69",
number = "6",
pages = "413-420",
doi = "10.2298/JSC0406413K"
}

Krstić, N., Bjelaković, M., Dabović, M., Lorenc, L.,& Pavlović, V. D.. (2004). Photochemical and Beckmann rearrangement of (Z)-cholest-4-en-6-one oxime. in Journal of the Serbian Chemical Society
Serbian Chemical Society., 69(6), 413-420.
https://doi.org/10.2298/JSC0406413K

Krstić N, Bjelaković M, Dabović M, Lorenc L, Pavlović VD. Photochemical and Beckmann rearrangement of (Z)-cholest-4-en-6-one oxime. in Journal of the Serbian Chemical Society. 2004;69(6):413-420.
doi:10.2298/JSC0406413K .

Krstić, Natalija, Bjelaković, Mira, Dabović, Milan, Lorenc, Ljubinka, Pavlović, Vladimir D., "Photochemical and Beckmann rearrangement of (Z)-cholest-4-en-6-one oxime" in Journal of the Serbian Chemical Society, 69, no. 6 (2004):413-420,
https://doi.org/10.2298/JSC0406413K . .

TY  - JOUR
AU  - Krstić, Natalija
AU  - Bjelaković, Mira
AU  - Lorenc, Ljubinka
AU  - Pavlović, Vladimir D.
PY  - 2003
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/109
AB  - 5-hydroxy-1-oxo-5α-cholestan-3β-yl acetate (11) was prepared in 5 steps starting from (E)-3β-acetoxy-5,10-seco-1(10)-cholesten-5-one (6). Treatment of the 1-oxo-5-hydroxy derivative 11 with lead tetraacetate (LTA) (under thermal or hypoiodite conditions) or with mercuric oxide/iodine (HgO/I2) reagent resulted in the oxidative β-fragmentation of the C(5)–C(10) bond affording 1,5-dioxo-5,10-secocholest-10(19)-en-3β-yl acetate (12), in different yields, depending on the reagent. Also the stereochemistry of the 1β,6β-cyclization product 13, formed by transannular cyclization of the 1,5-diketone 12 on silica gel, is discussed in this work.
AB  - Sintetizovan je 5-hidroksi-1-okso-5α-holestan-3β-il-acetata (11) u 5 faza polazeći od (E)- 3β-acetoksi-5,10-seko-1(10)-holesten-5-ona (6). Dejstvom olovo-tetraacetata (LTA) (pod termičkim ili hipojoditnim uslovima), ili merkuri-oksid/jodnog reagensa (HgO/I2) na 1-okso-5-hidroksi derivat 11, vrši se oksidativna β-fragmentacija njegove C(5)–C(10) veze, pri čemu se dobija 1,5-diokso-5,10-sekoholest-10(19)-en-3β-il-acetat (12), u različitim prinosima u zavisnosti od upotrebljenog reagensa. Takođe, diskutovana je stereohemija 1β,6β-ciklizacionog proizvoda 13, nastalog intramolekulskom ciklizacijom 1,5-diokso-5,10-seko jedinjenja 12 na silika gelu.
PB  - Serbian Chemical Society
T2  - Journal of the Serbian Chemical Society
T1  - Oxidative fragmentation of 5-hydroxy-1-oxo-5α-cholestan-3β-yl acetate
T1  - Oksidativne fragmentacije 5-hidroksi-1-okso-5α-holestan-3β-il-acetata
VL  - 68
IS  - 11
SP  - 785
EP  - 794
DO  - 10.2298/JSC0311785K
ER  - 

@article{
author = "Krstić, Natalija and Bjelaković, Mira and Lorenc, Ljubinka and Pavlović, Vladimir D.",
year = "2003",
abstract = "5-hydroxy-1-oxo-5α-cholestan-3β-yl acetate (11) was prepared in 5 steps starting from (E)-3β-acetoxy-5,10-seco-1(10)-cholesten-5-one (6). Treatment of the 1-oxo-5-hydroxy derivative 11 with lead tetraacetate (LTA) (under thermal or hypoiodite conditions) or with mercuric oxide/iodine (HgO/I2) reagent resulted in the oxidative β-fragmentation of the C(5)–C(10) bond affording 1,5-dioxo-5,10-secocholest-10(19)-en-3β-yl acetate (12), in different yields, depending on the reagent. Also the stereochemistry of the 1β,6β-cyclization product 13, formed by transannular cyclization of the 1,5-diketone 12 on silica gel, is discussed in this work., Sintetizovan je 5-hidroksi-1-okso-5α-holestan-3β-il-acetata (11) u 5 faza polazeći od (E)- 3β-acetoksi-5,10-seko-1(10)-holesten-5-ona (6). Dejstvom olovo-tetraacetata (LTA) (pod termičkim ili hipojoditnim uslovima), ili merkuri-oksid/jodnog reagensa (HgO/I2) na 1-okso-5-hidroksi derivat 11, vrši se oksidativna β-fragmentacija njegove C(5)–C(10) veze, pri čemu se dobija 1,5-diokso-5,10-sekoholest-10(19)-en-3β-il-acetat (12), u različitim prinosima u zavisnosti od upotrebljenog reagensa. Takođe, diskutovana je stereohemija 1β,6β-ciklizacionog proizvoda 13, nastalog intramolekulskom ciklizacijom 1,5-diokso-5,10-seko jedinjenja 12 na silika gelu.",
publisher = "Serbian Chemical Society",
journal = "Journal of the Serbian Chemical Society",
title = "Oxidative fragmentation of 5-hydroxy-1-oxo-5α-cholestan-3β-yl acetate, Oksidativne fragmentacije 5-hidroksi-1-okso-5α-holestan-3β-il-acetata",
volume = "68",
number = "11",
pages = "785-794",
doi = "10.2298/JSC0311785K"
}

Krstić, N., Bjelaković, M., Lorenc, L.,& Pavlović, V. D.. (2003). Oxidative fragmentation of 5-hydroxy-1-oxo-5α-cholestan-3β-yl acetate. in Journal of the Serbian Chemical Society
Serbian Chemical Society., 68(11), 785-794.
https://doi.org/10.2298/JSC0311785K

Krstić N, Bjelaković M, Lorenc L, Pavlović VD. Oxidative fragmentation of 5-hydroxy-1-oxo-5α-cholestan-3β-yl acetate. in Journal of the Serbian Chemical Society. 2003;68(11):785-794.
doi:10.2298/JSC0311785K .

Krstić, Natalija, Bjelaković, Mira, Lorenc, Ljubinka, Pavlović, Vladimir D., "Oxidative fragmentation of 5-hydroxy-1-oxo-5α-cholestan-3β-yl acetate" in Journal of the Serbian Chemical Society, 68, no. 11 (2003):785-794,
https://doi.org/10.2298/JSC0311785K . .

TY  - JOUR
AU  - Dabović, Milan
AU  - Petrović, Ivanka J.
AU  - Krstić, Natalija
AU  - Lorenc, Ljubinka
PY  - 2000
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/11
AB  - Expoxidation of cholesta-5,8-dien-3β-yl acetate (1) with peracids takes place preferentially at the more highly substituted Δ8-olefinic double bond to give: (a) with monoperphthalic acid, 8α,9α-epoxycholest-5-en-3β-yl acetate (2) (in 39 % yield) and 9α-hydroxy-5α,6α-epoxycholest-8(14)-en-3β-yl acetate (3) (in 30 % yield); and (b) with m-chloroperbenzoic acid, the 8α,9α-epoxide 2 (64 %) and 5α,6α-epoxy derivative 3 (20 %). Some chemical transformations of the obtained epoxides are described.
AB  - Epoksidacija holesta-5,8-dien-3β-il acetata (1) sa perkiselinama prvenstveno se odvija na više supstituisanoj Δ8-olefinskoj dvoguboj vezi pri čemu se dobija: (a) sa monoperftalnom kiselinom, 8α,9α-epoksiholest-5-en-3β-il acetat (2) (u prenosu od 39 %) i 9α-hidroksi-5α,6α-epoksiholest-8(14)-en-3β-il acetat (3) (u prenosu od 30 %); i (b) sa m-hlorperbenzoevom kiselinom, 8α,9α-epoksid 2 (u prenosu od 64 %) i 5α,6α-epoksi derivat 3 (u prenosu od 20 %). Opisane su i neke hemijske transformacije dobijenih epoksida.
PB  - Serbian Chemical Society
T2  - Journal of the Serbian Chemical Society
T1  - Peracids oxidation of cholesta-5,8-dien-3β-yl acetate
T1  - Oksidacija holesta-5,8-dien-3β-il acetata sa perkiselinama
VL  - 65
IS  - 11
SP  - 769
EP  - 772
UR  - https://hdl.handle.net/21.15107/rcub_cer_11
ER  - 

@article{
author = "Dabović, Milan and Petrović, Ivanka J. and Krstić, Natalija and Lorenc, Ljubinka",
year = "2000",
abstract = "Expoxidation of cholesta-5,8-dien-3β-yl acetate (1) with peracids takes place preferentially at the more highly substituted Δ8-olefinic double bond to give: (a) with monoperphthalic acid, 8α,9α-epoxycholest-5-en-3β-yl acetate (2) (in 39 % yield) and 9α-hydroxy-5α,6α-epoxycholest-8(14)-en-3β-yl acetate (3) (in 30 % yield); and (b) with m-chloroperbenzoic acid, the 8α,9α-epoxide 2 (64 %) and 5α,6α-epoxy derivative 3 (20 %). Some chemical transformations of the obtained epoxides are described., Epoksidacija holesta-5,8-dien-3β-il acetata (1) sa perkiselinama prvenstveno se odvija na više supstituisanoj Δ8-olefinskoj dvoguboj vezi pri čemu se dobija: (a) sa monoperftalnom kiselinom, 8α,9α-epoksiholest-5-en-3β-il acetat (2) (u prenosu od 39 %) i 9α-hidroksi-5α,6α-epoksiholest-8(14)-en-3β-il acetat (3) (u prenosu od 30 %); i (b) sa m-hlorperbenzoevom kiselinom, 8α,9α-epoksid 2 (u prenosu od 64 %) i 5α,6α-epoksi derivat 3 (u prenosu od 20 %). Opisane su i neke hemijske transformacije dobijenih epoksida.",
publisher = "Serbian Chemical Society",
journal = "Journal of the Serbian Chemical Society",
title = "Peracids oxidation of cholesta-5,8-dien-3β-yl acetate, Oksidacija holesta-5,8-dien-3β-il acetata sa perkiselinama",
volume = "65",
number = "11",
pages = "769-772",
url = "https://hdl.handle.net/21.15107/rcub_cer_11"
}

Dabović, M., Petrović, I. J., Krstić, N.,& Lorenc, L.. (2000). Peracids oxidation of cholesta-5,8-dien-3β-yl acetate. in Journal of the Serbian Chemical Society
Serbian Chemical Society., 65(11), 769-772.
https://hdl.handle.net/21.15107/rcub_cer_11

Dabović M, Petrović IJ, Krstić N, Lorenc L. Peracids oxidation of cholesta-5,8-dien-3β-yl acetate. in Journal of the Serbian Chemical Society. 2000;65(11):769-772.
https://hdl.handle.net/21.15107/rcub_cer_11 .

Dabović, Milan, Petrović, Ivanka J., Krstić, Natalija, Lorenc, Ljubinka, "Peracids oxidation of cholesta-5,8-dien-3β-yl acetate" in Journal of the Serbian Chemical Society, 65, no. 11 (2000):769-772,
https://hdl.handle.net/21.15107/rcub_cer_11 .

TY  - JOUR
AU  - Lorenc, Ljubinka B.
AU  - Pavlović, Vladimir
AU  - Juranić, Ivan
AU  - Mihailović, Milhailo Lj.
AU  - Bondarenko-Gheorghiu, Lidija G.
AU  - Krstić, Natalija
AU  - Dabović, Milan
PY  - 1999
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/4401
AB  - The thermal and acid-catalyzed intramolecular rearrangement of the (Z)- and (E)-cyclodecene-1,4-dione compounds deriving from steroids, 2a,b and 3a,b, respectively, proceeds stereoselectively to give the corresponding configurationally different spiro-γ-lactone derivatives, the (5R,9R)-isomers 4a,b (from the (Z)-cyclodecenediones 2a,b) and the (5R,9S)-isomers 5a,b (from the (E)-cyclodecenediones 3a,b). The semiempirical MNDOAM1 and PM3 molecular orbital methods were applied to elucidate the possible mechanistic pathway of the observed intramolecular process leading to the spiro-γ-lactone structures.
PB  - MDPI
T2  - Molecules
T1  - Stereoselective transformation of cyclodecene-1,4-dione systems, derived from steroids, to the corresponding spiro-g-lactones. A semiempirical MO Study
VL  - 4
IS  - 10
SP  - 272
EP  - 278
DO  - 10.3390/41000272
ER  - 

@article{
author = "Lorenc, Ljubinka B. and Pavlović, Vladimir and Juranić, Ivan and Mihailović, Milhailo Lj. and Bondarenko-Gheorghiu, Lidija G. and Krstić, Natalija and Dabović, Milan",
year = "1999",
abstract = "The thermal and acid-catalyzed intramolecular rearrangement of the (Z)- and (E)-cyclodecene-1,4-dione compounds deriving from steroids, 2a,b and 3a,b, respectively, proceeds stereoselectively to give the corresponding configurationally different spiro-γ-lactone derivatives, the (5R,9R)-isomers 4a,b (from the (Z)-cyclodecenediones 2a,b) and the (5R,9S)-isomers 5a,b (from the (E)-cyclodecenediones 3a,b). The semiempirical MNDOAM1 and PM3 molecular orbital methods were applied to elucidate the possible mechanistic pathway of the observed intramolecular process leading to the spiro-γ-lactone structures.",
publisher = "MDPI",
journal = "Molecules",
title = "Stereoselective transformation of cyclodecene-1,4-dione systems, derived from steroids, to the corresponding spiro-g-lactones. A semiempirical MO Study",
volume = "4",
number = "10",
pages = "272-278",
doi = "10.3390/41000272"
}

Lorenc, L. B., Pavlović, V., Juranić, I., Mihailović, M. Lj., Bondarenko-Gheorghiu, L. G., Krstić, N.,& Dabović, M.. (1999). Stereoselective transformation of cyclodecene-1,4-dione systems, derived from steroids, to the corresponding spiro-g-lactones. A semiempirical MO Study. in Molecules
MDPI., 4(10), 272-278.
https://doi.org/10.3390/41000272

Lorenc LB, Pavlović V, Juranić I, Mihailović ML, Bondarenko-Gheorghiu LG, Krstić N, Dabović M. Stereoselective transformation of cyclodecene-1,4-dione systems, derived from steroids, to the corresponding spiro-g-lactones. A semiempirical MO Study. in Molecules. 1999;4(10):272-278.
doi:10.3390/41000272 .

Lorenc, Ljubinka B., Pavlović, Vladimir, Juranić, Ivan, Mihailović, Milhailo Lj., Bondarenko-Gheorghiu, Lidija G., Krstić, Natalija, Dabović, Milan, "Stereoselective transformation of cyclodecene-1,4-dione systems, derived from steroids, to the corresponding spiro-g-lactones. A semiempirical MO Study" in Molecules, 4, no. 10 (1999):272-278,
https://doi.org/10.3390/41000272 . .

TY  - JOUR
AU  - Mihailović, Milhailo Lj.
AU  - Dabović, Milan
AU  - Pavlović, Vladimir D.
AU  - Krstić, Natalija
AU  - Lorenc, Ljubinka
PY  - 1997
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/2707
AB  - 5-Hydroxy-5α-cholest-8-en-3β-yl acetate (8) (prepared in 6 steps starting from 7-dehydrocholesteryl acetate (1) was transformed with ruthenium tetroxide to 5-hydroxy-8,9-dioxo-8,9-seco-5α-cholestan-3β-yl acetate (9). Treatment of the latter 8,9-seco-5-hydroxy derivative with lead tetraacetate (LTA) or mercuric oxide/iodine reagent (HgO/I2) resulted, instead of the expected oxidative β-fragmentation of its C(5)-C(10) bond, in the competing non-regio and non-stereoselective acetoxylation of the α-positions next to the 8- and 9-oxo functions (with LTA), and in the ≈ 82% recovery of the starting material (with HgO/I2). The results are discussed in terms of the strong hydrogen bonding which exists between the 5α-hydroxyl and the 8-oxo group.
PB  - Serbian Chemical Society
T2  - Journal of the Serbian Chemical Society
T1  - Synthesis and oxidative transformations of 5-hydroxy-5α-cholest-8-en-3β-yl acetate
VL  - 62
IS  - 9
SP  - 719
EP  - 726
UR  - https://hdl.handle.net/21.15107/rcub_cer_2707
ER  - 

@article{
author = "Mihailović, Milhailo Lj. and Dabović, Milan and Pavlović, Vladimir D. and Krstić, Natalija and Lorenc, Ljubinka",
year = "1997",
abstract = "5-Hydroxy-5α-cholest-8-en-3β-yl acetate (8) (prepared in 6 steps starting from 7-dehydrocholesteryl acetate (1) was transformed with ruthenium tetroxide to 5-hydroxy-8,9-dioxo-8,9-seco-5α-cholestan-3β-yl acetate (9). Treatment of the latter 8,9-seco-5-hydroxy derivative with lead tetraacetate (LTA) or mercuric oxide/iodine reagent (HgO/I2) resulted, instead of the expected oxidative β-fragmentation of its C(5)-C(10) bond, in the competing non-regio and non-stereoselective acetoxylation of the α-positions next to the 8- and 9-oxo functions (with LTA), and in the ≈ 82% recovery of the starting material (with HgO/I2). The results are discussed in terms of the strong hydrogen bonding which exists between the 5α-hydroxyl and the 8-oxo group.",
publisher = "Serbian Chemical Society",
journal = "Journal of the Serbian Chemical Society",
title = "Synthesis and oxidative transformations of 5-hydroxy-5α-cholest-8-en-3β-yl acetate",
volume = "62",
number = "9",
pages = "719-726",
url = "https://hdl.handle.net/21.15107/rcub_cer_2707"
}

Mihailović, M. Lj., Dabović, M., Pavlović, V. D., Krstić, N.,& Lorenc, L.. (1997). Synthesis and oxidative transformations of 5-hydroxy-5α-cholest-8-en-3β-yl acetate. in Journal of the Serbian Chemical Society
Serbian Chemical Society., 62(9), 719-726.
https://hdl.handle.net/21.15107/rcub_cer_2707

Mihailović ML, Dabović M, Pavlović VD, Krstić N, Lorenc L. Synthesis and oxidative transformations of 5-hydroxy-5α-cholest-8-en-3β-yl acetate. in Journal of the Serbian Chemical Society. 1997;62(9):719-726.
https://hdl.handle.net/21.15107/rcub_cer_2707 .

Mihailović, Milhailo Lj., Dabović, Milan, Pavlović, Vladimir D., Krstić, Natalija, Lorenc, Ljubinka, "Synthesis and oxidative transformations of 5-hydroxy-5α-cholest-8-en-3β-yl acetate" in Journal of the Serbian Chemical Society, 62, no. 9 (1997):719-726,
https://hdl.handle.net/21.15107/rcub_cer_2707 .