Serbian Academy of Sciences and Arts

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Serbian Academy of Sciences and Arts

Authors

Publications

Novel artesunate–pyrimidine-based hybrids with anticancer potential against multidrug-resistant cancer cells

Koračak, Ljiljana; Lupšić, Ema; Terzić-Jovanović, Nataša; Jovanović, Mirna; Novaković, Miroslav; Nedialkov, Paraskev; Trendafilova, Antoaneta; Zlatović, Mario; Pešić, Milica; Opsenica, Igor

(Royal Society of Chemistry, 2023)

TY  - JOUR
AU  - Koračak, Ljiljana
AU  - Lupšić, Ema
AU  - Terzić-Jovanović, Nataša
AU  - Jovanović, Mirna
AU  - Novaković, Miroslav
AU  - Nedialkov, Paraskev
AU  - Trendafilova, Antoaneta
AU  - Zlatović, Mario
AU  - Pešić, Milica
AU  - Opsenica, Igor
PY  - 2023
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/7172
AB  - The synthesis of 17 hybrid molecules, consisting of artesunate, a derivative of naturally occurring artemisinin, and synthetic 4-aryl-2-aminopyrimidines, is described. New compounds were designed to improve the parent compounds' cytotoxic properties, activity, and selectivity. The synthesized hybrid molecules (15a–f with ethylenediamine linker and 16a–k with piperazine linker), as well as their precursors – pyrimidine derivatives (13a–f and 14a–k), artemisinin, and artesunate, were tested on sensitive and multidrug-resistant (MDR) human non-small cell lung carcinoma (NSCLC) cells. All hybrid compounds with piperazine linker 16a–k were selective toward NSCLC cells and displayed IC50 values below 5 μM. Although they showed similar anticancer potency as artesunate, their selectivity against cancer cells was considerably improved. Importantly, 16h–k hybrid compounds were able to evade MDR phenotype, inhibit P-glycoprotein (P-gp) activity, and increase the sensitivity of MDR NSCLC cells to doxorubicin (DOX). The inhibition of P-gp activity induced by 16h–j was stronger than the one obtained with artesunate. Among these four hybrid compounds, 16k was the most potent anticancer agent with similar IC50 values of around 1.5 μM (for comparison – over 3.1 μM for artesunate) in sensitive and MDR NSCLC cells.
PB  - Royal Society of Chemistry
T2  - New Journal of Chemistry
T1  - Novel artesunate–pyrimidine-based hybrids with anticancer potential against multidrug-resistant cancer cells
VL  - 47
IS  - 14
SP  - 6844
EP  - 6855
DO  - 10.1039/D3NJ00427A
ER  - 
@article{
author = "Koračak, Ljiljana and Lupšić, Ema and Terzić-Jovanović, Nataša and Jovanović, Mirna and Novaković, Miroslav and Nedialkov, Paraskev and Trendafilova, Antoaneta and Zlatović, Mario and Pešić, Milica and Opsenica, Igor",
year = "2023",
abstract = "The synthesis of 17 hybrid molecules, consisting of artesunate, a derivative of naturally occurring artemisinin, and synthetic 4-aryl-2-aminopyrimidines, is described. New compounds were designed to improve the parent compounds' cytotoxic properties, activity, and selectivity. The synthesized hybrid molecules (15a–f with ethylenediamine linker and 16a–k with piperazine linker), as well as their precursors – pyrimidine derivatives (13a–f and 14a–k), artemisinin, and artesunate, were tested on sensitive and multidrug-resistant (MDR) human non-small cell lung carcinoma (NSCLC) cells. All hybrid compounds with piperazine linker 16a–k were selective toward NSCLC cells and displayed IC50 values below 5 μM. Although they showed similar anticancer potency as artesunate, their selectivity against cancer cells was considerably improved. Importantly, 16h–k hybrid compounds were able to evade MDR phenotype, inhibit P-glycoprotein (P-gp) activity, and increase the sensitivity of MDR NSCLC cells to doxorubicin (DOX). The inhibition of P-gp activity induced by 16h–j was stronger than the one obtained with artesunate. Among these four hybrid compounds, 16k was the most potent anticancer agent with similar IC50 values of around 1.5 μM (for comparison – over 3.1 μM for artesunate) in sensitive and MDR NSCLC cells.",
publisher = "Royal Society of Chemistry",
journal = "New Journal of Chemistry",
title = "Novel artesunate–pyrimidine-based hybrids with anticancer potential against multidrug-resistant cancer cells",
volume = "47",
number = "14",
pages = "6844-6855",
doi = "10.1039/D3NJ00427A"
}
Koračak, L., Lupšić, E., Terzić-Jovanović, N., Jovanović, M., Novaković, M., Nedialkov, P., Trendafilova, A., Zlatović, M., Pešić, M.,& Opsenica, I.. (2023). Novel artesunate–pyrimidine-based hybrids with anticancer potential against multidrug-resistant cancer cells. in New Journal of Chemistry
Royal Society of Chemistry., 47(14), 6844-6855.
https://doi.org/10.1039/D3NJ00427A
Koračak L, Lupšić E, Terzić-Jovanović N, Jovanović M, Novaković M, Nedialkov P, Trendafilova A, Zlatović M, Pešić M, Opsenica I. Novel artesunate–pyrimidine-based hybrids with anticancer potential against multidrug-resistant cancer cells. in New Journal of Chemistry. 2023;47(14):6844-6855.
doi:10.1039/D3NJ00427A .
Koračak, Ljiljana, Lupšić, Ema, Terzić-Jovanović, Nataša, Jovanović, Mirna, Novaković, Miroslav, Nedialkov, Paraskev, Trendafilova, Antoaneta, Zlatović, Mario, Pešić, Milica, Opsenica, Igor, "Novel artesunate–pyrimidine-based hybrids with anticancer potential against multidrug-resistant cancer cells" in New Journal of Chemistry, 47, no. 14 (2023):6844-6855,
https://doi.org/10.1039/D3NJ00427A . .
3
1
1

New Steroidal 4-Aminoquinolines Antagonize Botulinum Neurotoxin Serotype A in Mouse Embryonic Stem Cell Derived Motor Neurons in Postintoxication Model

Konstantinović, Jelena M.; Kiris, Erkan; Kota, Krishna P.; Kugelman-Tonos, Johanny; Videnović, Milica; Cazares, Lisa H.; Terzić-Jovanović, Nataša; Verbić, Tatjana; Anđelković, Boban D.; Duplantier, Allen J.; Bavari, Sina; Šolaja, Bogdan

(American Chemical Society (ACS), 2018)

TY  - JOUR
AU  - Konstantinović, Jelena M.
AU  - Kiris, Erkan
AU  - Kota, Krishna P.
AU  - Kugelman-Tonos, Johanny
AU  - Videnović, Milica
AU  - Cazares, Lisa H.
AU  - Terzić-Jovanović, Nataša
AU  - Verbić, Tatjana
AU  - Anđelković, Boban D.
AU  - Duplantier, Allen J.
AU  - Bavari, Sina
AU  - Šolaja, Bogdan
PY  - 2018
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/2325
AB  - The synthesis and inhibitory potencies against botulinum neurotoxin serotype A light chain (BoNT/A LC) using in vitro HPLC based enzymatic assay for various steroidal, benzothiophene, thiophene, and adamantane 4-aminoquinoline derivatives are described. In addition, the compounds were evaluated for the activity against BoNT/A holotoxin in mouse embryonic stem cell derived motor neurons. Steroidal derivative 16 showed remarkable protection (up to 89% of uncleaved SNAP-25) even when administered 30 min postintoxication. This appears to be the first example of LC inhibitors antagonizing BoNT intoxication in mouse embryonic stem cell derived motor neurons (mES-MNs) in a postexposure model. Oral administration of 16 was well tolerated in the mouse up to 600 mg/kg, q.d. Although adequate unbound drug levels were not achieved at this dose, the favorable in vitro ADMET results strongly support further work in this series.
PB  - American Chemical Society (ACS)
T2  - Journal of Medicinal Chemistry
T1  - New Steroidal 4-Aminoquinolines Antagonize Botulinum Neurotoxin Serotype A in Mouse Embryonic Stem Cell Derived Motor Neurons in Postintoxication Model
VL  - 61
IS  - 4
SP  - 1595
EP  - 1608
DO  - 10.1021/acs.jmedchem.7b01710
ER  - 
@article{
author = "Konstantinović, Jelena M. and Kiris, Erkan and Kota, Krishna P. and Kugelman-Tonos, Johanny and Videnović, Milica and Cazares, Lisa H. and Terzić-Jovanović, Nataša and Verbić, Tatjana and Anđelković, Boban D. and Duplantier, Allen J. and Bavari, Sina and Šolaja, Bogdan",
year = "2018",
abstract = "The synthesis and inhibitory potencies against botulinum neurotoxin serotype A light chain (BoNT/A LC) using in vitro HPLC based enzymatic assay for various steroidal, benzothiophene, thiophene, and adamantane 4-aminoquinoline derivatives are described. In addition, the compounds were evaluated for the activity against BoNT/A holotoxin in mouse embryonic stem cell derived motor neurons. Steroidal derivative 16 showed remarkable protection (up to 89% of uncleaved SNAP-25) even when administered 30 min postintoxication. This appears to be the first example of LC inhibitors antagonizing BoNT intoxication in mouse embryonic stem cell derived motor neurons (mES-MNs) in a postexposure model. Oral administration of 16 was well tolerated in the mouse up to 600 mg/kg, q.d. Although adequate unbound drug levels were not achieved at this dose, the favorable in vitro ADMET results strongly support further work in this series.",
publisher = "American Chemical Society (ACS)",
journal = "Journal of Medicinal Chemistry",
title = "New Steroidal 4-Aminoquinolines Antagonize Botulinum Neurotoxin Serotype A in Mouse Embryonic Stem Cell Derived Motor Neurons in Postintoxication Model",
volume = "61",
number = "4",
pages = "1595-1608",
doi = "10.1021/acs.jmedchem.7b01710"
}
Konstantinović, J. M., Kiris, E., Kota, K. P., Kugelman-Tonos, J., Videnović, M., Cazares, L. H., Terzić-Jovanović, N., Verbić, T., Anđelković, B. D., Duplantier, A. J., Bavari, S.,& Šolaja, B.. (2018). New Steroidal 4-Aminoquinolines Antagonize Botulinum Neurotoxin Serotype A in Mouse Embryonic Stem Cell Derived Motor Neurons in Postintoxication Model. in Journal of Medicinal Chemistry
American Chemical Society (ACS)., 61(4), 1595-1608.
https://doi.org/10.1021/acs.jmedchem.7b01710
Konstantinović JM, Kiris E, Kota KP, Kugelman-Tonos J, Videnović M, Cazares LH, Terzić-Jovanović N, Verbić T, Anđelković BD, Duplantier AJ, Bavari S, Šolaja B. New Steroidal 4-Aminoquinolines Antagonize Botulinum Neurotoxin Serotype A in Mouse Embryonic Stem Cell Derived Motor Neurons in Postintoxication Model. in Journal of Medicinal Chemistry. 2018;61(4):1595-1608.
doi:10.1021/acs.jmedchem.7b01710 .
Konstantinović, Jelena M., Kiris, Erkan, Kota, Krishna P., Kugelman-Tonos, Johanny, Videnović, Milica, Cazares, Lisa H., Terzić-Jovanović, Nataša, Verbić, Tatjana, Anđelković, Boban D., Duplantier, Allen J., Bavari, Sina, Šolaja, Bogdan, "New Steroidal 4-Aminoquinolines Antagonize Botulinum Neurotoxin Serotype A in Mouse Embryonic Stem Cell Derived Motor Neurons in Postintoxication Model" in Journal of Medicinal Chemistry, 61, no. 4 (2018):1595-1608,
https://doi.org/10.1021/acs.jmedchem.7b01710 . .
7
4
7

New Steroidal 4-Aminoquinolines Antagonize Botulinum Neurotoxin Serotype A in Mouse Embryonic Stem Cell Derived Motor Neurons in Postintoxication Model

Konstantinović, Jelena M.; Kiris, Erkan; Kota, Krishna P.; Kugelman-Tonos, Johanny; Videnović, Milica; Cazares, Lisa H.; Terzić-Jovanović, Nataša; Verbić, Tatjana; Anđelković, Boban D.; Duplantier, Allen J.; Bavari, Sina; Šolaja, Bogdan

(American Chemical Society (ACS), 2018)

TY  - JOUR
AU  - Konstantinović, Jelena M.
AU  - Kiris, Erkan
AU  - Kota, Krishna P.
AU  - Kugelman-Tonos, Johanny
AU  - Videnović, Milica
AU  - Cazares, Lisa H.
AU  - Terzić-Jovanović, Nataša
AU  - Verbić, Tatjana
AU  - Anđelković, Boban D.
AU  - Duplantier, Allen J.
AU  - Bavari, Sina
AU  - Šolaja, Bogdan
PY  - 2018
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/2935
AB  - The synthesis and inhibitory potencies against botulinum neurotoxin serotype A light chain (BoNT/A LC) using in vitro HPLC based enzymatic assay for various steroidal, benzothiophene, thiophene, and adamantane 4-aminoquinoline derivatives are described. In addition, the compounds were evaluated for the activity against BoNT/A holotoxin in mouse embryonic stem cell derived motor neurons. Steroidal derivative 16 showed remarkable protection (up to 89% of uncleaved SNAP-25) even when administered 30 min postintoxication. This appears to be the first example of LC inhibitors antagonizing BoNT intoxication in mouse embryonic stem cell derived motor neurons (mES-MNs) in a postexposure model. Oral administration of 16 was well tolerated in the mouse up to 600 mg/kg, q.d. Although adequate unbound drug levels were not achieved at this dose, the favorable in vitro ADMET results strongly support further work in this series.
PB  - American Chemical Society (ACS)
T2  - Journal of Medicinal Chemistry
T1  - New Steroidal 4-Aminoquinolines Antagonize Botulinum Neurotoxin Serotype A in Mouse Embryonic Stem Cell Derived Motor Neurons in Postintoxication Model
VL  - 61
IS  - 4
SP  - 1595
EP  - 1608
DO  - 10.1021/acs.jmedchem.7b01710
ER  - 
@article{
author = "Konstantinović, Jelena M. and Kiris, Erkan and Kota, Krishna P. and Kugelman-Tonos, Johanny and Videnović, Milica and Cazares, Lisa H. and Terzić-Jovanović, Nataša and Verbić, Tatjana and Anđelković, Boban D. and Duplantier, Allen J. and Bavari, Sina and Šolaja, Bogdan",
year = "2018",
abstract = "The synthesis and inhibitory potencies against botulinum neurotoxin serotype A light chain (BoNT/A LC) using in vitro HPLC based enzymatic assay for various steroidal, benzothiophene, thiophene, and adamantane 4-aminoquinoline derivatives are described. In addition, the compounds were evaluated for the activity against BoNT/A holotoxin in mouse embryonic stem cell derived motor neurons. Steroidal derivative 16 showed remarkable protection (up to 89% of uncleaved SNAP-25) even when administered 30 min postintoxication. This appears to be the first example of LC inhibitors antagonizing BoNT intoxication in mouse embryonic stem cell derived motor neurons (mES-MNs) in a postexposure model. Oral administration of 16 was well tolerated in the mouse up to 600 mg/kg, q.d. Although adequate unbound drug levels were not achieved at this dose, the favorable in vitro ADMET results strongly support further work in this series.",
publisher = "American Chemical Society (ACS)",
journal = "Journal of Medicinal Chemistry",
title = "New Steroidal 4-Aminoquinolines Antagonize Botulinum Neurotoxin Serotype A in Mouse Embryonic Stem Cell Derived Motor Neurons in Postintoxication Model",
volume = "61",
number = "4",
pages = "1595-1608",
doi = "10.1021/acs.jmedchem.7b01710"
}
Konstantinović, J. M., Kiris, E., Kota, K. P., Kugelman-Tonos, J., Videnović, M., Cazares, L. H., Terzić-Jovanović, N., Verbić, T., Anđelković, B. D., Duplantier, A. J., Bavari, S.,& Šolaja, B.. (2018). New Steroidal 4-Aminoquinolines Antagonize Botulinum Neurotoxin Serotype A in Mouse Embryonic Stem Cell Derived Motor Neurons in Postintoxication Model. in Journal of Medicinal Chemistry
American Chemical Society (ACS)., 61(4), 1595-1608.
https://doi.org/10.1021/acs.jmedchem.7b01710
Konstantinović JM, Kiris E, Kota KP, Kugelman-Tonos J, Videnović M, Cazares LH, Terzić-Jovanović N, Verbić T, Anđelković BD, Duplantier AJ, Bavari S, Šolaja B. New Steroidal 4-Aminoquinolines Antagonize Botulinum Neurotoxin Serotype A in Mouse Embryonic Stem Cell Derived Motor Neurons in Postintoxication Model. in Journal of Medicinal Chemistry. 2018;61(4):1595-1608.
doi:10.1021/acs.jmedchem.7b01710 .
Konstantinović, Jelena M., Kiris, Erkan, Kota, Krishna P., Kugelman-Tonos, Johanny, Videnović, Milica, Cazares, Lisa H., Terzić-Jovanović, Nataša, Verbić, Tatjana, Anđelković, Boban D., Duplantier, Allen J., Bavari, Sina, Šolaja, Bogdan, "New Steroidal 4-Aminoquinolines Antagonize Botulinum Neurotoxin Serotype A in Mouse Embryonic Stem Cell Derived Motor Neurons in Postintoxication Model" in Journal of Medicinal Chemistry, 61, no. 4 (2018):1595-1608,
https://doi.org/10.1021/acs.jmedchem.7b01710 . .
7
4
7

Supporting Information I for: "New Steroidal 4-Aminoquinolines Antagonize Botulinum Neurotoxin Serotype A in Mouse Embryonic Stem Cell Derived Motor Neurons in Postintoxication Model"

Konstantinović, Jelena M.; Kiris, Erkan; Kota, Krishna P.; Kugelman-Tonos, Johanny; Videnović, Milica; Cazares, Lisa H.; Terzić-Jovanović, Nataša; Verbić, Tatjana; Anđelković, Boban D.; Duplantier, Allen J.; Bavari, Sina; Šolaja, Bogdan

(American Chemical Society (ACS), 2018)

TY  - DATA
AU  - Konstantinović, Jelena M.
AU  - Kiris, Erkan
AU  - Kota, Krishna P.
AU  - Kugelman-Tonos, Johanny
AU  - Videnović, Milica
AU  - Cazares, Lisa H.
AU  - Terzić-Jovanović, Nataša
AU  - Verbić, Tatjana
AU  - Anđelković, Boban D.
AU  - Duplantier, Allen J.
AU  - Bavari, Sina
AU  - Šolaja, Bogdan
PY  - 2018
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/4515
AB  - Inhibitory activities against BoNT/A LC and holotoxin in proteolytic and cell-based assay for all tested compounds; fluorescence and UV–vis spectra for determination of 16 binding to HSA and AGP; ligand interaction diagrams, docking scores, and docking–in vitro inhibitory activity correlations; spectral and analytical data for all synthesized compounds; detailed procedures for the determination of the HPLC purity.
PB  - American Chemical Society (ACS)
T2  - Journal of Medicinal Chemistry
T1  - Supporting Information I for: "New Steroidal 4-Aminoquinolines Antagonize Botulinum Neurotoxin Serotype A in Mouse Embryonic Stem Cell Derived Motor Neurons in Postintoxication Model"
DO  - 10.1021/acs.jmedchem.7b01710.s001
ER  - 
@misc{
author = "Konstantinović, Jelena M. and Kiris, Erkan and Kota, Krishna P. and Kugelman-Tonos, Johanny and Videnović, Milica and Cazares, Lisa H. and Terzić-Jovanović, Nataša and Verbić, Tatjana and Anđelković, Boban D. and Duplantier, Allen J. and Bavari, Sina and Šolaja, Bogdan",
year = "2018",
abstract = "Inhibitory activities against BoNT/A LC and holotoxin in proteolytic and cell-based assay for all tested compounds; fluorescence and UV–vis spectra for determination of 16 binding to HSA and AGP; ligand interaction diagrams, docking scores, and docking–in vitro inhibitory activity correlations; spectral and analytical data for all synthesized compounds; detailed procedures for the determination of the HPLC purity.",
publisher = "American Chemical Society (ACS)",
journal = "Journal of Medicinal Chemistry",
title = "Supporting Information I for: "New Steroidal 4-Aminoquinolines Antagonize Botulinum Neurotoxin Serotype A in Mouse Embryonic Stem Cell Derived Motor Neurons in Postintoxication Model"",
doi = "10.1021/acs.jmedchem.7b01710.s001"
}
Konstantinović, J. M., Kiris, E., Kota, K. P., Kugelman-Tonos, J., Videnović, M., Cazares, L. H., Terzić-Jovanović, N., Verbić, T., Anđelković, B. D., Duplantier, A. J., Bavari, S.,& Šolaja, B.. (2018). Supporting Information I for: "New Steroidal 4-Aminoquinolines Antagonize Botulinum Neurotoxin Serotype A in Mouse Embryonic Stem Cell Derived Motor Neurons in Postintoxication Model". in Journal of Medicinal Chemistry
American Chemical Society (ACS)..
https://doi.org/10.1021/acs.jmedchem.7b01710.s001
Konstantinović JM, Kiris E, Kota KP, Kugelman-Tonos J, Videnović M, Cazares LH, Terzić-Jovanović N, Verbić T, Anđelković BD, Duplantier AJ, Bavari S, Šolaja B. Supporting Information I for: "New Steroidal 4-Aminoquinolines Antagonize Botulinum Neurotoxin Serotype A in Mouse Embryonic Stem Cell Derived Motor Neurons in Postintoxication Model". in Journal of Medicinal Chemistry. 2018;.
doi:10.1021/acs.jmedchem.7b01710.s001 .
Konstantinović, Jelena M., Kiris, Erkan, Kota, Krishna P., Kugelman-Tonos, Johanny, Videnović, Milica, Cazares, Lisa H., Terzić-Jovanović, Nataša, Verbić, Tatjana, Anđelković, Boban D., Duplantier, Allen J., Bavari, Sina, Šolaja, Bogdan, "Supporting Information I for: "New Steroidal 4-Aminoquinolines Antagonize Botulinum Neurotoxin Serotype A in Mouse Embryonic Stem Cell Derived Motor Neurons in Postintoxication Model"" in Journal of Medicinal Chemistry (2018),
https://doi.org/10.1021/acs.jmedchem.7b01710.s001 . .

Supporting Information II for: "New Steroidal 4-Aminoquinolines Antagonize Botulinum Neurotoxin Serotype A in Mouse Embryonic Stem Cell Derived Motor Neurons in Postintoxication Model"

Konstantinović, Jelena M.; Kiris, Erkan; Kota, Krishna P.; Kugelman-Tonos, Johanny; Videnović, Milica; Cazares, Lisa H.; Terzić-Jovanović, Nataša; Verbić, Tatjana; Anđelković, Boban D.; Duplantier, Allen J.; Bavari, Sina; Šolaja, Bogdan

(American Chemical Society (ACS), 2018)

TY  - DATA
AU  - Konstantinović, Jelena M.
AU  - Kiris, Erkan
AU  - Kota, Krishna P.
AU  - Kugelman-Tonos, Johanny
AU  - Videnović, Milica
AU  - Cazares, Lisa H.
AU  - Terzić-Jovanović, Nataša
AU  - Verbić, Tatjana
AU  - Anđelković, Boban D.
AU  - Duplantier, Allen J.
AU  - Bavari, Sina
AU  - Šolaja, Bogdan
PY  - 2018
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/4516
AB  - NMR spectra and HPLC purity spectra of all tested compounds
PB  - American Chemical Society (ACS)
T2  - Journal of Medicinal Chemistry
T1  - Supporting Information II for: "New Steroidal 4-Aminoquinolines Antagonize Botulinum Neurotoxin Serotype A in Mouse Embryonic Stem Cell Derived Motor Neurons in Postintoxication Model"
DO  - 10.1021/acs.jmedchem.7b01710.s002
ER  - 
@misc{
author = "Konstantinović, Jelena M. and Kiris, Erkan and Kota, Krishna P. and Kugelman-Tonos, Johanny and Videnović, Milica and Cazares, Lisa H. and Terzić-Jovanović, Nataša and Verbić, Tatjana and Anđelković, Boban D. and Duplantier, Allen J. and Bavari, Sina and Šolaja, Bogdan",
year = "2018",
abstract = "NMR spectra and HPLC purity spectra of all tested compounds",
publisher = "American Chemical Society (ACS)",
journal = "Journal of Medicinal Chemistry",
title = "Supporting Information II for: "New Steroidal 4-Aminoquinolines Antagonize Botulinum Neurotoxin Serotype A in Mouse Embryonic Stem Cell Derived Motor Neurons in Postintoxication Model"",
doi = "10.1021/acs.jmedchem.7b01710.s002"
}
Konstantinović, J. M., Kiris, E., Kota, K. P., Kugelman-Tonos, J., Videnović, M., Cazares, L. H., Terzić-Jovanović, N., Verbić, T., Anđelković, B. D., Duplantier, A. J., Bavari, S.,& Šolaja, B.. (2018). Supporting Information II for: "New Steroidal 4-Aminoquinolines Antagonize Botulinum Neurotoxin Serotype A in Mouse Embryonic Stem Cell Derived Motor Neurons in Postintoxication Model". in Journal of Medicinal Chemistry
American Chemical Society (ACS)..
https://doi.org/10.1021/acs.jmedchem.7b01710.s002
Konstantinović JM, Kiris E, Kota KP, Kugelman-Tonos J, Videnović M, Cazares LH, Terzić-Jovanović N, Verbić T, Anđelković BD, Duplantier AJ, Bavari S, Šolaja B. Supporting Information II for: "New Steroidal 4-Aminoquinolines Antagonize Botulinum Neurotoxin Serotype A in Mouse Embryonic Stem Cell Derived Motor Neurons in Postintoxication Model". in Journal of Medicinal Chemistry. 2018;.
doi:10.1021/acs.jmedchem.7b01710.s002 .
Konstantinović, Jelena M., Kiris, Erkan, Kota, Krishna P., Kugelman-Tonos, Johanny, Videnović, Milica, Cazares, Lisa H., Terzić-Jovanović, Nataša, Verbić, Tatjana, Anđelković, Boban D., Duplantier, Allen J., Bavari, Sina, Šolaja, Bogdan, "Supporting Information II for: "New Steroidal 4-Aminoquinolines Antagonize Botulinum Neurotoxin Serotype A in Mouse Embryonic Stem Cell Derived Motor Neurons in Postintoxication Model"" in Journal of Medicinal Chemistry (2018),
https://doi.org/10.1021/acs.jmedchem.7b01710.s002 . .

Supporting Information III for: "New Steroidal 4-Aminoquinolines Antagonize Botulinum Neurotoxin Serotype A in Mouse Embryonic Stem Cell Derived Motor Neurons in Postintoxication Model"

Konstantinović, Jelena M.; Kiris, Erkan; Kota, Krishna P.; Kugelman-Tonos, Johanny; Videnović, Milica; Cazares, Lisa H.; Terzić-Jovanović, Nataša; Verbić, Tatjana; Anđelković, Boban D.; Duplantier, Allen J.; Bavari, Sina; Šolaja, Bogdan

(American Chemical Society (ACS), 2018)

TY  - DATA
AU  - Konstantinović, Jelena M.
AU  - Kiris, Erkan
AU  - Kota, Krishna P.
AU  - Kugelman-Tonos, Johanny
AU  - Videnović, Milica
AU  - Cazares, Lisa H.
AU  - Terzić-Jovanović, Nataša
AU  - Verbić, Tatjana
AU  - Anđelković, Boban D.
AU  - Duplantier, Allen J.
AU  - Bavari, Sina
AU  - Šolaja, Bogdan
PY  - 2018
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/4517
AB  - Molecular formula strings (smiles) and additional data: In vitro proteolytic assay % inh BoNT/A LC at 20 uM; In vitro proteolytic assay IC50 (uM); mES-MNs pre intoxication % of full length SNAP-25 (10 uM; 20 uM); mES-MNs post intoxication at 20 uM % of full length SNAP-25 (30 min; 60 min)
PB  - American Chemical Society (ACS)
T2  - Journal of Medicinal Chemistry
T1  - Supporting Information III for: "New Steroidal 4-Aminoquinolines Antagonize Botulinum Neurotoxin Serotype A in Mouse Embryonic Stem Cell Derived Motor Neurons in Postintoxication Model"
DO  - 10.1021/acs.jmedchem.7b01710.s003
ER  - 
@misc{
author = "Konstantinović, Jelena M. and Kiris, Erkan and Kota, Krishna P. and Kugelman-Tonos, Johanny and Videnović, Milica and Cazares, Lisa H. and Terzić-Jovanović, Nataša and Verbić, Tatjana and Anđelković, Boban D. and Duplantier, Allen J. and Bavari, Sina and Šolaja, Bogdan",
year = "2018",
abstract = "Molecular formula strings (smiles) and additional data: In vitro proteolytic assay % inh BoNT/A LC at 20 uM; In vitro proteolytic assay IC50 (uM); mES-MNs pre intoxication % of full length SNAP-25 (10 uM; 20 uM); mES-MNs post intoxication at 20 uM % of full length SNAP-25 (30 min; 60 min)",
publisher = "American Chemical Society (ACS)",
journal = "Journal of Medicinal Chemistry",
title = "Supporting Information III for: "New Steroidal 4-Aminoquinolines Antagonize Botulinum Neurotoxin Serotype A in Mouse Embryonic Stem Cell Derived Motor Neurons in Postintoxication Model"",
doi = "10.1021/acs.jmedchem.7b01710.s003"
}
Konstantinović, J. M., Kiris, E., Kota, K. P., Kugelman-Tonos, J., Videnović, M., Cazares, L. H., Terzić-Jovanović, N., Verbić, T., Anđelković, B. D., Duplantier, A. J., Bavari, S.,& Šolaja, B.. (2018). Supporting Information III for: "New Steroidal 4-Aminoquinolines Antagonize Botulinum Neurotoxin Serotype A in Mouse Embryonic Stem Cell Derived Motor Neurons in Postintoxication Model". in Journal of Medicinal Chemistry
American Chemical Society (ACS)..
https://doi.org/10.1021/acs.jmedchem.7b01710.s003
Konstantinović JM, Kiris E, Kota KP, Kugelman-Tonos J, Videnović M, Cazares LH, Terzić-Jovanović N, Verbić T, Anđelković BD, Duplantier AJ, Bavari S, Šolaja B. Supporting Information III for: "New Steroidal 4-Aminoquinolines Antagonize Botulinum Neurotoxin Serotype A in Mouse Embryonic Stem Cell Derived Motor Neurons in Postintoxication Model". in Journal of Medicinal Chemistry. 2018;.
doi:10.1021/acs.jmedchem.7b01710.s003 .
Konstantinović, Jelena M., Kiris, Erkan, Kota, Krishna P., Kugelman-Tonos, Johanny, Videnović, Milica, Cazares, Lisa H., Terzić-Jovanović, Nataša, Verbić, Tatjana, Anđelković, Boban D., Duplantier, Allen J., Bavari, Sina, Šolaja, Bogdan, "Supporting Information III for: "New Steroidal 4-Aminoquinolines Antagonize Botulinum Neurotoxin Serotype A in Mouse Embryonic Stem Cell Derived Motor Neurons in Postintoxication Model"" in Journal of Medicinal Chemistry (2018),
https://doi.org/10.1021/acs.jmedchem.7b01710.s003 . .

Antibacterial and antifungal properties of guanylhydrazones

Ajdačić, Vladimir; Lazić, Jelena; Mojicevic, Marija; Šegan, Sandra; Nikodinović-Runić, Jasmina; Opsenica, Igor

(Serbian Chemical Soc, Belgrade, 2017)

TY  - JOUR
AU  - Ajdačić, Vladimir
AU  - Lazić, Jelena
AU  - Mojicevic, Marija
AU  - Šegan, Sandra
AU  - Nikodinović-Runić, Jasmina
AU  - Opsenica, Igor
PY  - 2017
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/2138
AB  - A series of novel guanylhydrazones were designed, synthesized and characterized. All the compounds were screened for their antibacterial and antifungal activity. Compounds 26 and 27 showed excellent antibacterial activities against Staphylococcus aureus ATCC 25923 and Micrococcus luteus ATCC 379 with minimal inhibitory concentrations of 4 ae g mL(-1), and good antifungal activity against Candida parapsilosis ATCC 22019. These results suggested that the selected guanylhydrazones could serve as promising leads for improved antimicrobial development.
PB  - Serbian Chemical Soc, Belgrade
T2  - Journal of the Serbian Chemical Society
T1  - Antibacterial and antifungal properties of guanylhydrazones
VL  - 82
IS  - 6
SP  - 641
EP  - 649
DO  - 10.2298/JSC170213033A
ER  - 
@article{
author = "Ajdačić, Vladimir and Lazić, Jelena and Mojicevic, Marija and Šegan, Sandra and Nikodinović-Runić, Jasmina and Opsenica, Igor",
year = "2017",
abstract = "A series of novel guanylhydrazones were designed, synthesized and characterized. All the compounds were screened for their antibacterial and antifungal activity. Compounds 26 and 27 showed excellent antibacterial activities against Staphylococcus aureus ATCC 25923 and Micrococcus luteus ATCC 379 with minimal inhibitory concentrations of 4 ae g mL(-1), and good antifungal activity against Candida parapsilosis ATCC 22019. These results suggested that the selected guanylhydrazones could serve as promising leads for improved antimicrobial development.",
publisher = "Serbian Chemical Soc, Belgrade",
journal = "Journal of the Serbian Chemical Society",
title = "Antibacterial and antifungal properties of guanylhydrazones",
volume = "82",
number = "6",
pages = "641-649",
doi = "10.2298/JSC170213033A"
}
Ajdačić, V., Lazić, J., Mojicevic, M., Šegan, S., Nikodinović-Runić, J.,& Opsenica, I.. (2017). Antibacterial and antifungal properties of guanylhydrazones. in Journal of the Serbian Chemical Society
Serbian Chemical Soc, Belgrade., 82(6), 641-649.
https://doi.org/10.2298/JSC170213033A
Ajdačić V, Lazić J, Mojicevic M, Šegan S, Nikodinović-Runić J, Opsenica I. Antibacterial and antifungal properties of guanylhydrazones. in Journal of the Serbian Chemical Society. 2017;82(6):641-649.
doi:10.2298/JSC170213033A .
Ajdačić, Vladimir, Lazić, Jelena, Mojicevic, Marija, Šegan, Sandra, Nikodinović-Runić, Jasmina, Opsenica, Igor, "Antibacterial and antifungal properties of guanylhydrazones" in Journal of the Serbian Chemical Society, 82, no. 6 (2017):641-649,
https://doi.org/10.2298/JSC170213033A . .
3
3
3

Synthesis and anti-Candida activity of novel benzothiepino[3,2-c]pyridine derivatives

Bozinovic, Nina; Šegan, Sandra; Vojnovic, Sandra; Pavić, Aleksandar; Šolaja, Bogdan; Nikodinović-Runić, Jasmina; Opsenica, Igor

(Wiley, Hoboken, 2016)

TY  - JOUR
AU  - Bozinovic, Nina
AU  - Šegan, Sandra
AU  - Vojnovic, Sandra
AU  - Pavić, Aleksandar
AU  - Šolaja, Bogdan
AU  - Nikodinović-Runić, Jasmina
AU  - Opsenica, Igor
PY  - 2016
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/1887
AB  - A novel series of thiepine derivatives were synthesized and evaluated as potential antimicrobials. All the synthesized compounds were evaluated for their antimicrobial activities in vitro against the fungi Candida albicans (ATCC 10231), C.parapsilosis (clinical isolate), Gram-negative bacterium Pseudomonas aeruginosa (ATCC 44752), and Gram-positive bacterium Staphylococcus aureus (ATCC 25923). Synthesized compounds showed higher antifungal activity than antibacterial activity, indicating that they could be used as selective antimicrobials. Selected thiepines efficiently inhibited Candida hyphae formation, a trait necessary for their pathogenicity. Thiepine 8-phenyl[1]benzothiepino[3,2-c]pyridine (16) efficiently killed Candida albicans at 15.6g/mL and showed no embryotoxicity at 75g/mL. Derivative 8-[4-(4,5-dihydro-1H-imidazol-2-yl)phenyl][1]benzothiepino[3,2-c]pyridine (23) caused significant hemolysis and in vitro DNA interaction. The position of the phenyl ring was essential for the antifungal activity, while the electronic effects of the substituents did not significantly influence activity. Results obtained from in vivo embryotoxicity on zebrafish (Danio rerio) encourage further structure optimizations.
PB  - Wiley, Hoboken
T2  - Chemical Biology & Drug Design
T1  - Synthesis and anti-Candida activity of novel benzothiepino[3,2-c]pyridine derivatives
VL  - 88
IS  - 6
SP  - 795
EP  - 806
DO  - 10.1111/cbdd.12809
ER  - 
@article{
author = "Bozinovic, Nina and Šegan, Sandra and Vojnovic, Sandra and Pavić, Aleksandar and Šolaja, Bogdan and Nikodinović-Runić, Jasmina and Opsenica, Igor",
year = "2016",
abstract = "A novel series of thiepine derivatives were synthesized and evaluated as potential antimicrobials. All the synthesized compounds were evaluated for their antimicrobial activities in vitro against the fungi Candida albicans (ATCC 10231), C.parapsilosis (clinical isolate), Gram-negative bacterium Pseudomonas aeruginosa (ATCC 44752), and Gram-positive bacterium Staphylococcus aureus (ATCC 25923). Synthesized compounds showed higher antifungal activity than antibacterial activity, indicating that they could be used as selective antimicrobials. Selected thiepines efficiently inhibited Candida hyphae formation, a trait necessary for their pathogenicity. Thiepine 8-phenyl[1]benzothiepino[3,2-c]pyridine (16) efficiently killed Candida albicans at 15.6g/mL and showed no embryotoxicity at 75g/mL. Derivative 8-[4-(4,5-dihydro-1H-imidazol-2-yl)phenyl][1]benzothiepino[3,2-c]pyridine (23) caused significant hemolysis and in vitro DNA interaction. The position of the phenyl ring was essential for the antifungal activity, while the electronic effects of the substituents did not significantly influence activity. Results obtained from in vivo embryotoxicity on zebrafish (Danio rerio) encourage further structure optimizations.",
publisher = "Wiley, Hoboken",
journal = "Chemical Biology & Drug Design",
title = "Synthesis and anti-Candida activity of novel benzothiepino[3,2-c]pyridine derivatives",
volume = "88",
number = "6",
pages = "795-806",
doi = "10.1111/cbdd.12809"
}
Bozinovic, N., Šegan, S., Vojnovic, S., Pavić, A., Šolaja, B., Nikodinović-Runić, J.,& Opsenica, I.. (2016). Synthesis and anti-Candida activity of novel benzothiepino[3,2-c]pyridine derivatives. in Chemical Biology & Drug Design
Wiley, Hoboken., 88(6), 795-806.
https://doi.org/10.1111/cbdd.12809
Bozinovic N, Šegan S, Vojnovic S, Pavić A, Šolaja B, Nikodinović-Runić J, Opsenica I. Synthesis and anti-Candida activity of novel benzothiepino[3,2-c]pyridine derivatives. in Chemical Biology & Drug Design. 2016;88(6):795-806.
doi:10.1111/cbdd.12809 .
Bozinovic, Nina, Šegan, Sandra, Vojnovic, Sandra, Pavić, Aleksandar, Šolaja, Bogdan, Nikodinović-Runić, Jasmina, Opsenica, Igor, "Synthesis and anti-Candida activity of novel benzothiepino[3,2-c]pyridine derivatives" in Chemical Biology & Drug Design, 88, no. 6 (2016):795-806,
https://doi.org/10.1111/cbdd.12809 . .
10
8
7
10

Reinvestigating Old Pharmacophores: Are 4-Aminoquinolines and Tetraoxanes Potential Two-Stage Antimalarials?

Terzić-Jovanović, Nataša; Konstantinović, Jelena M.; Tot, Miklos; Burojevic, Jovana; Djurkovic-Djakovic, Olgica; Srbljanović, Jelena; Štajner, Tijana; Verbić, Tatjana; Zlatović, Mario; Machado, Marta; Albuquerque, Ines S; Prudencio, Miguel; Sciotii, Richard J; Pecic, Stevan; DAlessandro, Sarah; Taramelli, Donatella; Šolaja, Bogdan

(American Chemical Society (ACS), 2016)

TY  - JOUR
AU  - Terzić-Jovanović, Nataša
AU  - Konstantinović, Jelena M.
AU  - Tot, Miklos
AU  - Burojevic, Jovana
AU  - Djurkovic-Djakovic, Olgica
AU  - Srbljanović, Jelena
AU  - Štajner, Tijana
AU  - Verbić, Tatjana
AU  - Zlatović, Mario
AU  - Machado, Marta
AU  - Albuquerque, Ines S
AU  - Prudencio, Miguel
AU  - Sciotii, Richard J
AU  - Pecic, Stevan
AU  - DAlessandro, Sarah
AU  - Taramelli, Donatella
AU  - Šolaja, Bogdan
PY  - 2016
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/1953
AB  - The syntheses and antiplasmodial activities of various substituted aminoquinolines coupled to an adamantane carrier are described. The compounds exhibited pronounced in vitro and in vivo activity against Plasmodium berghei in the Thompson test. Tethering a fluorine atom to the aminoquinoline C(3) position afforded fluoroaminoquinolines that act as intrahepatocytic parasite inhibitors, with compound 25 having an IC50 = 0.31 mu M and reducing the liver load in mice by up to 92% at 80 mg/kg dose. Screening our peroxides as inhibitors of liver stage infection revealed that the tetraoxane pharmacophore itself is also an excellent liver stage P. berghei inhibitor (78: IC50 = 0.33 mu M). Up to 91% reduction of the parasite liver load in mice was achieved at 100 mg/kg. Examination of tetraoxane 78 against the transgenic 3D7 strain expressing luciferase under a gametocyte-specific promoter revealed its activity against stage IV-V Plasmodium falciparum gametocytes (IC50 = 1.16 +/- 0.37 mu M). To the best of our knowledge, compounds 25 and 78 are the first examples of either an 4-aminoquinoline or a tetraoxane liver stage inhibitors.
PB  - American Chemical Society (ACS)
T2  - Journal of Medicinal Chemistry
T1  - Reinvestigating Old Pharmacophores: Are 4-Aminoquinolines and Tetraoxanes Potential Two-Stage Antimalarials?
VL  - 59
IS  - 1
SP  - 264
EP  - 281
DO  - 10.1021/acs.jmedchem.5b01374
ER  - 
@article{
author = "Terzić-Jovanović, Nataša and Konstantinović, Jelena M. and Tot, Miklos and Burojevic, Jovana and Djurkovic-Djakovic, Olgica and Srbljanović, Jelena and Štajner, Tijana and Verbić, Tatjana and Zlatović, Mario and Machado, Marta and Albuquerque, Ines S and Prudencio, Miguel and Sciotii, Richard J and Pecic, Stevan and DAlessandro, Sarah and Taramelli, Donatella and Šolaja, Bogdan",
year = "2016",
abstract = "The syntheses and antiplasmodial activities of various substituted aminoquinolines coupled to an adamantane carrier are described. The compounds exhibited pronounced in vitro and in vivo activity against Plasmodium berghei in the Thompson test. Tethering a fluorine atom to the aminoquinoline C(3) position afforded fluoroaminoquinolines that act as intrahepatocytic parasite inhibitors, with compound 25 having an IC50 = 0.31 mu M and reducing the liver load in mice by up to 92% at 80 mg/kg dose. Screening our peroxides as inhibitors of liver stage infection revealed that the tetraoxane pharmacophore itself is also an excellent liver stage P. berghei inhibitor (78: IC50 = 0.33 mu M). Up to 91% reduction of the parasite liver load in mice was achieved at 100 mg/kg. Examination of tetraoxane 78 against the transgenic 3D7 strain expressing luciferase under a gametocyte-specific promoter revealed its activity against stage IV-V Plasmodium falciparum gametocytes (IC50 = 1.16 +/- 0.37 mu M). To the best of our knowledge, compounds 25 and 78 are the first examples of either an 4-aminoquinoline or a tetraoxane liver stage inhibitors.",
publisher = "American Chemical Society (ACS)",
journal = "Journal of Medicinal Chemistry",
title = "Reinvestigating Old Pharmacophores: Are 4-Aminoquinolines and Tetraoxanes Potential Two-Stage Antimalarials?",
volume = "59",
number = "1",
pages = "264-281",
doi = "10.1021/acs.jmedchem.5b01374"
}
Terzić-Jovanović, N., Konstantinović, J. M., Tot, M., Burojevic, J., Djurkovic-Djakovic, O., Srbljanović, J., Štajner, T., Verbić, T., Zlatović, M., Machado, M., Albuquerque, I. S., Prudencio, M., Sciotii, R. J., Pecic, S., DAlessandro, S., Taramelli, D.,& Šolaja, B.. (2016). Reinvestigating Old Pharmacophores: Are 4-Aminoquinolines and Tetraoxanes Potential Two-Stage Antimalarials?. in Journal of Medicinal Chemistry
American Chemical Society (ACS)., 59(1), 264-281.
https://doi.org/10.1021/acs.jmedchem.5b01374
Terzić-Jovanović N, Konstantinović JM, Tot M, Burojevic J, Djurkovic-Djakovic O, Srbljanović J, Štajner T, Verbić T, Zlatović M, Machado M, Albuquerque IS, Prudencio M, Sciotii RJ, Pecic S, DAlessandro S, Taramelli D, Šolaja B. Reinvestigating Old Pharmacophores: Are 4-Aminoquinolines and Tetraoxanes Potential Two-Stage Antimalarials?. in Journal of Medicinal Chemistry. 2016;59(1):264-281.
doi:10.1021/acs.jmedchem.5b01374 .
Terzić-Jovanović, Nataša, Konstantinović, Jelena M., Tot, Miklos, Burojevic, Jovana, Djurkovic-Djakovic, Olgica, Srbljanović, Jelena, Štajner, Tijana, Verbić, Tatjana, Zlatović, Mario, Machado, Marta, Albuquerque, Ines S, Prudencio, Miguel, Sciotii, Richard J, Pecic, Stevan, DAlessandro, Sarah, Taramelli, Donatella, Šolaja, Bogdan, "Reinvestigating Old Pharmacophores: Are 4-Aminoquinolines and Tetraoxanes Potential Two-Stage Antimalarials?" in Journal of Medicinal Chemistry, 59, no. 1 (2016):264-281,
https://doi.org/10.1021/acs.jmedchem.5b01374 . .
1
31
20
30

Synthesis and anti-Candida activity of novel benzothiepino[3,2-c]pyridine derivatives

Bozinovic, Nina; Šegan, Sandra; Vojnovic, Sandra; Pavić, Aleksandar; Šolaja, Bogdan; Nikodinović-Runić, Jasmina; Opsenica, Igor

(Wiley, Hoboken, 2016)

TY  - JOUR
AU  - Bozinovic, Nina
AU  - Šegan, Sandra
AU  - Vojnovic, Sandra
AU  - Pavić, Aleksandar
AU  - Šolaja, Bogdan
AU  - Nikodinović-Runić, Jasmina
AU  - Opsenica, Igor
PY  - 2016
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/3192
AB  - A novel series of thiepine derivatives were synthesized and evaluated as potential antimicrobials. All the synthesized compounds were evaluated for their antimicrobial activities in vitro against the fungi Candida albicans (ATCC 10231), C.parapsilosis (clinical isolate), Gram-negative bacterium Pseudomonas aeruginosa (ATCC 44752), and Gram-positive bacterium Staphylococcus aureus (ATCC 25923). Synthesized compounds showed higher antifungal activity than antibacterial activity, indicating that they could be used as selective antimicrobials. Selected thiepines efficiently inhibited Candida hyphae formation, a trait necessary for their pathogenicity. Thiepine 8-phenyl[1]benzothiepino[3,2-c]pyridine (16) efficiently killed Candida albicans at 15.6g/mL and showed no embryotoxicity at 75g/mL. Derivative 8-[4-(4,5-dihydro-1H-imidazol-2-yl)phenyl][1]benzothiepino[3,2-c]pyridine (23) caused significant hemolysis and in vitro DNA interaction. The position of the phenyl ring was essential for the antifungal activity, while the electronic effects of the substituents did not significantly influence activity. Results obtained from in vivo embryotoxicity on zebrafish (Danio rerio) encourage further structure optimizations.
PB  - Wiley, Hoboken
T2  - Chemical Biology & Drug Design
T1  - Synthesis and anti-Candida activity of novel benzothiepino[3,2-c]pyridine derivatives
VL  - 88
IS  - 6
SP  - 795
EP  - 806
DO  - 10.1111/cbdd.12809
ER  - 
@article{
author = "Bozinovic, Nina and Šegan, Sandra and Vojnovic, Sandra and Pavić, Aleksandar and Šolaja, Bogdan and Nikodinović-Runić, Jasmina and Opsenica, Igor",
year = "2016",
abstract = "A novel series of thiepine derivatives were synthesized and evaluated as potential antimicrobials. All the synthesized compounds were evaluated for their antimicrobial activities in vitro against the fungi Candida albicans (ATCC 10231), C.parapsilosis (clinical isolate), Gram-negative bacterium Pseudomonas aeruginosa (ATCC 44752), and Gram-positive bacterium Staphylococcus aureus (ATCC 25923). Synthesized compounds showed higher antifungal activity than antibacterial activity, indicating that they could be used as selective antimicrobials. Selected thiepines efficiently inhibited Candida hyphae formation, a trait necessary for their pathogenicity. Thiepine 8-phenyl[1]benzothiepino[3,2-c]pyridine (16) efficiently killed Candida albicans at 15.6g/mL and showed no embryotoxicity at 75g/mL. Derivative 8-[4-(4,5-dihydro-1H-imidazol-2-yl)phenyl][1]benzothiepino[3,2-c]pyridine (23) caused significant hemolysis and in vitro DNA interaction. The position of the phenyl ring was essential for the antifungal activity, while the electronic effects of the substituents did not significantly influence activity. Results obtained from in vivo embryotoxicity on zebrafish (Danio rerio) encourage further structure optimizations.",
publisher = "Wiley, Hoboken",
journal = "Chemical Biology & Drug Design",
title = "Synthesis and anti-Candida activity of novel benzothiepino[3,2-c]pyridine derivatives",
volume = "88",
number = "6",
pages = "795-806",
doi = "10.1111/cbdd.12809"
}
Bozinovic, N., Šegan, S., Vojnovic, S., Pavić, A., Šolaja, B., Nikodinović-Runić, J.,& Opsenica, I.. (2016). Synthesis and anti-Candida activity of novel benzothiepino[3,2-c]pyridine derivatives. in Chemical Biology & Drug Design
Wiley, Hoboken., 88(6), 795-806.
https://doi.org/10.1111/cbdd.12809
Bozinovic N, Šegan S, Vojnovic S, Pavić A, Šolaja B, Nikodinović-Runić J, Opsenica I. Synthesis and anti-Candida activity of novel benzothiepino[3,2-c]pyridine derivatives. in Chemical Biology & Drug Design. 2016;88(6):795-806.
doi:10.1111/cbdd.12809 .
Bozinovic, Nina, Šegan, Sandra, Vojnovic, Sandra, Pavić, Aleksandar, Šolaja, Bogdan, Nikodinović-Runić, Jasmina, Opsenica, Igor, "Synthesis and anti-Candida activity of novel benzothiepino[3,2-c]pyridine derivatives" in Chemical Biology & Drug Design, 88, no. 6 (2016):795-806,
https://doi.org/10.1111/cbdd.12809 . .
10
8
7
10

Decarbonylative Dibromination of 5-Phenylthiophene-2-carbaldehyde with Bromine

Ajdačić, Vladimir; Stepanović, Stepan; Zlatović, Mario; Gruden, Maja; Opsenica, Igor

(Georg Thieme Verlag Kg, Stuttgart, 2016)

TY  - JOUR
AU  - Ajdačić, Vladimir
AU  - Stepanović, Stepan
AU  - Zlatović, Mario
AU  - Gruden, Maja
AU  - Opsenica, Igor
PY  - 2016
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/1951
AB  - The decarbonylative dibromination of 2-thiophenecarboxaldehyde derivatives with bromine under mild conditions is developed. The mechanism for the decarbonylation is investigated by experimental and instrumental techniques and is extended by a computational study. Alongside removal of the formyl group, this method enables functionalization of the starting compounds in a single reaction step, which can be further exploited for the synthesis of 2,5-diaryl-3-bromothiophenes and 2,3,5-triarylthiophenes.
PB  - Georg Thieme Verlag Kg, Stuttgart
T2  - Synthesis
T1  - Decarbonylative Dibromination of 5-Phenylthiophene-2-carbaldehyde with Bromine
VL  - 48
IS  - 24
SP  - 4423
EP  - 4430
DO  - 10.1055/s-0035-1562615
ER  - 
@article{
author = "Ajdačić, Vladimir and Stepanović, Stepan and Zlatović, Mario and Gruden, Maja and Opsenica, Igor",
year = "2016",
abstract = "The decarbonylative dibromination of 2-thiophenecarboxaldehyde derivatives with bromine under mild conditions is developed. The mechanism for the decarbonylation is investigated by experimental and instrumental techniques and is extended by a computational study. Alongside removal of the formyl group, this method enables functionalization of the starting compounds in a single reaction step, which can be further exploited for the synthesis of 2,5-diaryl-3-bromothiophenes and 2,3,5-triarylthiophenes.",
publisher = "Georg Thieme Verlag Kg, Stuttgart",
journal = "Synthesis",
title = "Decarbonylative Dibromination of 5-Phenylthiophene-2-carbaldehyde with Bromine",
volume = "48",
number = "24",
pages = "4423-4430",
doi = "10.1055/s-0035-1562615"
}
Ajdačić, V., Stepanović, S., Zlatović, M., Gruden, M.,& Opsenica, I.. (2016). Decarbonylative Dibromination of 5-Phenylthiophene-2-carbaldehyde with Bromine. in Synthesis
Georg Thieme Verlag Kg, Stuttgart., 48(24), 4423-4430.
https://doi.org/10.1055/s-0035-1562615
Ajdačić V, Stepanović S, Zlatović M, Gruden M, Opsenica I. Decarbonylative Dibromination of 5-Phenylthiophene-2-carbaldehyde with Bromine. in Synthesis. 2016;48(24):4423-4430.
doi:10.1055/s-0035-1562615 .
Ajdačić, Vladimir, Stepanović, Stepan, Zlatović, Mario, Gruden, Maja, Opsenica, Igor, "Decarbonylative Dibromination of 5-Phenylthiophene-2-carbaldehyde with Bromine" in Synthesis, 48, no. 24 (2016):4423-4430,
https://doi.org/10.1055/s-0035-1562615 . .
3
2
4

Synthesis and antimicrobial activity of azepine and thiepine derivatives

Bozinovic, Nina; Novaković, Irena; Kostić Rajačić, Slađana; Opsenica, Igor; Šolaja, Bogdan

(Serbian Chemical Soc, Belgrade, 2015)

TY  - JOUR
AU  - Bozinovic, Nina
AU  - Novaković, Irena
AU  - Kostić Rajačić, Slađana
AU  - Opsenica, Igor
AU  - Šolaja, Bogdan
PY  - 2015
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/1702
AB  - A series of new pyridobenzazepine and pyridobenzothiepine derivatives was synthesized by Pd-catalyzed formation of C-N and C-S bonds. All synthesized compounds were tested for their in vitro antimicrobial activity. The pyridobenzazepine derivatives showed better antibacterial and antifungal activity than the corresponding dipyridoazepine analogue. Among the synthesized azepines, derivative 8 displayed potent activity against the tested bacteria (MIC ranged 39-78 mu g mL(-1)), while azepine 12 showed promising antifungal activity (MIC ranged 156-313 mu g mL(-1)). The synthesized thiepine derivatives exhibited weak antibacterial activity, but showed pronounced antifungal activity.
PB  - Serbian Chemical Soc, Belgrade
T2  - Journal of the Serbian Chemical Society
T1  - Synthesis and antimicrobial activity of azepine and thiepine derivatives
VL  - 80
IS  - 7
SP  - 839
EP  - 852
DO  - 10.2298/JSC150116013B
ER  - 
@article{
author = "Bozinovic, Nina and Novaković, Irena and Kostić Rajačić, Slađana and Opsenica, Igor and Šolaja, Bogdan",
year = "2015",
abstract = "A series of new pyridobenzazepine and pyridobenzothiepine derivatives was synthesized by Pd-catalyzed formation of C-N and C-S bonds. All synthesized compounds were tested for their in vitro antimicrobial activity. The pyridobenzazepine derivatives showed better antibacterial and antifungal activity than the corresponding dipyridoazepine analogue. Among the synthesized azepines, derivative 8 displayed potent activity against the tested bacteria (MIC ranged 39-78 mu g mL(-1)), while azepine 12 showed promising antifungal activity (MIC ranged 156-313 mu g mL(-1)). The synthesized thiepine derivatives exhibited weak antibacterial activity, but showed pronounced antifungal activity.",
publisher = "Serbian Chemical Soc, Belgrade",
journal = "Journal of the Serbian Chemical Society",
title = "Synthesis and antimicrobial activity of azepine and thiepine derivatives",
volume = "80",
number = "7",
pages = "839-852",
doi = "10.2298/JSC150116013B"
}
Bozinovic, N., Novaković, I., Kostić Rajačić, S., Opsenica, I.,& Šolaja, B.. (2015). Synthesis and antimicrobial activity of azepine and thiepine derivatives. in Journal of the Serbian Chemical Society
Serbian Chemical Soc, Belgrade., 80(7), 839-852.
https://doi.org/10.2298/JSC150116013B
Bozinovic N, Novaković I, Kostić Rajačić S, Opsenica I, Šolaja B. Synthesis and antimicrobial activity of azepine and thiepine derivatives. in Journal of the Serbian Chemical Society. 2015;80(7):839-852.
doi:10.2298/JSC150116013B .
Bozinovic, Nina, Novaković, Irena, Kostić Rajačić, Slađana, Opsenica, Igor, Šolaja, Bogdan, "Synthesis and antimicrobial activity of azepine and thiepine derivatives" in Journal of the Serbian Chemical Society, 80, no. 7 (2015):839-852,
https://doi.org/10.2298/JSC150116013B . .
1
10
6
10

The synthesis of single phase WC nanoparticles/C composite by solid state reaction involving nitrogen-rich carbonized polyaniline

Gavrilov, Nemanja; Pasti, Igor; Krstić, Jugoslav; Mitrić, Miodrag; Ciric-Marjanovic, Gordana; Mentus, Slavko

(Elsevier Sci Ltd, Oxford, 2013)

TY  - JOUR
AU  - Gavrilov, Nemanja
AU  - Pasti, Igor
AU  - Krstić, Jugoslav
AU  - Mitrić, Miodrag
AU  - Ciric-Marjanovic, Gordana
AU  - Mentus, Slavko
PY  - 2013
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/1261
AB  - Single phase tungsten carbide nanoparticles (WC-NPs), (mean particle diameter 5.4 nm), distributed over carbonized polyaniline (C-PANT) nanotubes/nanosheets were synthesized by a solid state reaction between WO3 and nitrogen-rich carbonized polyaniline at 1000 degrees C in a reducing atmosphere. The resulting composite was characterized by X-ray diffractometry, electron microscopy, thermogravimetry in oxidizing and reduction atmospheres and elemental analysis. We suggested that the synthesis of WC as a single phase was facilitated by reactive C atoms with dangling bonds, formed upon nitrogen removal.
PB  - Elsevier Sci Ltd, Oxford
T2  - Ceramics International
T1  - The synthesis of single phase WC nanoparticles/C composite by solid state reaction involving nitrogen-rich carbonized polyaniline
VL  - 39
IS  - 8
SP  - 8761
EP  - 8765
DO  - 10.1016/j.ceramint.2013.04.062
ER  - 
@article{
author = "Gavrilov, Nemanja and Pasti, Igor and Krstić, Jugoslav and Mitrić, Miodrag and Ciric-Marjanovic, Gordana and Mentus, Slavko",
year = "2013",
abstract = "Single phase tungsten carbide nanoparticles (WC-NPs), (mean particle diameter 5.4 nm), distributed over carbonized polyaniline (C-PANT) nanotubes/nanosheets were synthesized by a solid state reaction between WO3 and nitrogen-rich carbonized polyaniline at 1000 degrees C in a reducing atmosphere. The resulting composite was characterized by X-ray diffractometry, electron microscopy, thermogravimetry in oxidizing and reduction atmospheres and elemental analysis. We suggested that the synthesis of WC as a single phase was facilitated by reactive C atoms with dangling bonds, formed upon nitrogen removal.",
publisher = "Elsevier Sci Ltd, Oxford",
journal = "Ceramics International",
title = "The synthesis of single phase WC nanoparticles/C composite by solid state reaction involving nitrogen-rich carbonized polyaniline",
volume = "39",
number = "8",
pages = "8761-8765",
doi = "10.1016/j.ceramint.2013.04.062"
}
Gavrilov, N., Pasti, I., Krstić, J., Mitrić, M., Ciric-Marjanovic, G.,& Mentus, S.. (2013). The synthesis of single phase WC nanoparticles/C composite by solid state reaction involving nitrogen-rich carbonized polyaniline. in Ceramics International
Elsevier Sci Ltd, Oxford., 39(8), 8761-8765.
https://doi.org/10.1016/j.ceramint.2013.04.062
Gavrilov N, Pasti I, Krstić J, Mitrić M, Ciric-Marjanovic G, Mentus S. The synthesis of single phase WC nanoparticles/C composite by solid state reaction involving nitrogen-rich carbonized polyaniline. in Ceramics International. 2013;39(8):8761-8765.
doi:10.1016/j.ceramint.2013.04.062 .
Gavrilov, Nemanja, Pasti, Igor, Krstić, Jugoslav, Mitrić, Miodrag, Ciric-Marjanovic, Gordana, Mentus, Slavko, "The synthesis of single phase WC nanoparticles/C composite by solid state reaction involving nitrogen-rich carbonized polyaniline" in Ceramics International, 39, no. 8 (2013):8761-8765,
https://doi.org/10.1016/j.ceramint.2013.04.062 . .
9
10
11

Artemisinins and synthetic peroxides as highly efficient antimalarials

Opsenica, Dejan; Šolaja, Bogdan

(Soc Chemists Technologists Madeconia, Skopje, 2012)

TY  - JOUR
AU  - Opsenica, Dejan
AU  - Šolaja, Bogdan
PY  - 2012
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/1088
AB  - Malaria is devastating disease and global public health problem, with nearly half world population exposed to risk. Illness is caused by five Plasmodium species, P falciparum, P ovale, P viva; P malaria and P knowlesi, from which P falciparum is the most serious one causing cerebral malaria and is the major reason for malaria mortality. Vaccine against malaria is not expected in the near future and chemotherapy remains as most feasible alternative for treatment of the disease. The development of widespread drug-resistance to chloroquine (CQ), the most successful antimalarial drug up to date, has resulted in severe health issues for countries in malaria endemic regions. Organic peroxides, like artemisinins, 1,2,4-trioxanes, 1,2,4-trioxolanes, 1,2,4,5-tetraoxanes and their chimeras, are the best choice for malaria treatment nowadays. These therapeutics are fast acting, non-toxic, low costing and without reported data of parasite resistance. Stability of peroxide bonds enables synthetic comfort and resulting in diversity of synthesized structures. The most important classes of peroxide antimalarials with promising representatives are reviewed and possible mechanisms of action were presented in details.
PB  - Soc Chemists Technologists Madeconia, Skopje
T2  - Macedonian Journal of Chemistry and Chemical Engineering
T1  - Artemisinins and synthetic peroxides as highly efficient antimalarials
VL  - 31
IS  - 2
SP  - 137
EP  - 182
UR  - https://hdl.handle.net/21.15107/rcub_cherry_1579
ER  - 
@article{
author = "Opsenica, Dejan and Šolaja, Bogdan",
year = "2012",
abstract = "Malaria is devastating disease and global public health problem, with nearly half world population exposed to risk. Illness is caused by five Plasmodium species, P falciparum, P ovale, P viva; P malaria and P knowlesi, from which P falciparum is the most serious one causing cerebral malaria and is the major reason for malaria mortality. Vaccine against malaria is not expected in the near future and chemotherapy remains as most feasible alternative for treatment of the disease. The development of widespread drug-resistance to chloroquine (CQ), the most successful antimalarial drug up to date, has resulted in severe health issues for countries in malaria endemic regions. Organic peroxides, like artemisinins, 1,2,4-trioxanes, 1,2,4-trioxolanes, 1,2,4,5-tetraoxanes and their chimeras, are the best choice for malaria treatment nowadays. These therapeutics are fast acting, non-toxic, low costing and without reported data of parasite resistance. Stability of peroxide bonds enables synthetic comfort and resulting in diversity of synthesized structures. The most important classes of peroxide antimalarials with promising representatives are reviewed and possible mechanisms of action were presented in details.",
publisher = "Soc Chemists Technologists Madeconia, Skopje",
journal = "Macedonian Journal of Chemistry and Chemical Engineering",
title = "Artemisinins and synthetic peroxides as highly efficient antimalarials",
volume = "31",
number = "2",
pages = "137-182",
url = "https://hdl.handle.net/21.15107/rcub_cherry_1579"
}
Opsenica, D.,& Šolaja, B.. (2012). Artemisinins and synthetic peroxides as highly efficient antimalarials. in Macedonian Journal of Chemistry and Chemical Engineering
Soc Chemists Technologists Madeconia, Skopje., 31(2), 137-182.
https://hdl.handle.net/21.15107/rcub_cherry_1579
Opsenica D, Šolaja B. Artemisinins and synthetic peroxides as highly efficient antimalarials. in Macedonian Journal of Chemistry and Chemical Engineering. 2012;31(2):137-182.
https://hdl.handle.net/21.15107/rcub_cherry_1579 .
Opsenica, Dejan, Šolaja, Bogdan, "Artemisinins and synthetic peroxides as highly efficient antimalarials" in Macedonian Journal of Chemistry and Chemical Engineering, 31, no. 2 (2012):137-182,
https://hdl.handle.net/21.15107/rcub_cherry_1579 .
7
9

A Chemotype That Inhibits Three Unrelated Pathogenic Targets: The Botulinum Neurotoxin Serotype A Light Chain, P. falciparum Malaria, and the Ebola Filovirus

Opsenica, Igor; Burnett, James C.; Gussio, Rick; Opsenica, Dejan; Todorović, Nina; Lanteri, Charlotte A.; Sciotti, Richard J.; Gettayacamin, Montip; Basilico, Nicoletta; Taramelli, Donatella; Nuss, Jonathan E.; Wanner, Laura; Panchal, Rekha G.; Šolaja, Bogdan; Bavari, Sina

(American Chemical Society (ACS), 2011)

TY  - JOUR
AU  - Opsenica, Igor
AU  - Burnett, James C.
AU  - Gussio, Rick
AU  - Opsenica, Dejan
AU  - Todorović, Nina
AU  - Lanteri, Charlotte A.
AU  - Sciotti, Richard J.
AU  - Gettayacamin, Montip
AU  - Basilico, Nicoletta
AU  - Taramelli, Donatella
AU  - Nuss, Jonathan E.
AU  - Wanner, Laura
AU  - Panchal, Rekha G.
AU  - Šolaja, Bogdan
AU  - Bavari, Sina
PY  - 2011
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/901
AB  - A 1,7-bis(alkylamino)diazachrysene-based small molecule was previously identified as an inhibitor of the botulinum neurotoxin serotype A light chain metalloprotease. Subsequently, a variety of derivatives of this chemotype were synthesized to develop structure activity relationships, and all are inhibitors of the BoNT/A LC. Three-dimensional analyses indicated that half of the originally discovered 1,7-DAAC structure superimposed well with 4-amino-7-chloroquinolinebased antimalarial agents. This observation led to the discovery that several of the 1,7-DAAC derivatives are potent in vitro inhibitors of Plasmodium falciparum and, in general, are more efficacious against CQ-resistant strains than against CQ-susceptible strains. In addition, by inhibiting beta-hematin formation, the most efficacious 1,7-DAAC-based antimalarials employ a mechanism of action analogous to that of 4,7-ACQ-based antimalarials and are well tolerated by normal cells. One candidate was also effective when administered orally in a rodent-based malaria model. Finally, the 1,7-DAAC-based derivatives were examined for Ebola filovirus inhibition in an assay employing Vero76 cells, and three provided promising antiviral activities and acceptably low toxicities.
PB  - American Chemical Society (ACS)
T2  - Journal of Medicinal Chemistry
T1  - A Chemotype That Inhibits Three Unrelated Pathogenic Targets: The Botulinum Neurotoxin Serotype A Light Chain, P. falciparum Malaria, and the Ebola Filovirus
VL  - 54
IS  - 5
SP  - 1157
EP  - 1169
DO  - 10.1021/jm100938u
ER  - 
@article{
author = "Opsenica, Igor and Burnett, James C. and Gussio, Rick and Opsenica, Dejan and Todorović, Nina and Lanteri, Charlotte A. and Sciotti, Richard J. and Gettayacamin, Montip and Basilico, Nicoletta and Taramelli, Donatella and Nuss, Jonathan E. and Wanner, Laura and Panchal, Rekha G. and Šolaja, Bogdan and Bavari, Sina",
year = "2011",
abstract = "A 1,7-bis(alkylamino)diazachrysene-based small molecule was previously identified as an inhibitor of the botulinum neurotoxin serotype A light chain metalloprotease. Subsequently, a variety of derivatives of this chemotype were synthesized to develop structure activity relationships, and all are inhibitors of the BoNT/A LC. Three-dimensional analyses indicated that half of the originally discovered 1,7-DAAC structure superimposed well with 4-amino-7-chloroquinolinebased antimalarial agents. This observation led to the discovery that several of the 1,7-DAAC derivatives are potent in vitro inhibitors of Plasmodium falciparum and, in general, are more efficacious against CQ-resistant strains than against CQ-susceptible strains. In addition, by inhibiting beta-hematin formation, the most efficacious 1,7-DAAC-based antimalarials employ a mechanism of action analogous to that of 4,7-ACQ-based antimalarials and are well tolerated by normal cells. One candidate was also effective when administered orally in a rodent-based malaria model. Finally, the 1,7-DAAC-based derivatives were examined for Ebola filovirus inhibition in an assay employing Vero76 cells, and three provided promising antiviral activities and acceptably low toxicities.",
publisher = "American Chemical Society (ACS)",
journal = "Journal of Medicinal Chemistry",
title = "A Chemotype That Inhibits Three Unrelated Pathogenic Targets: The Botulinum Neurotoxin Serotype A Light Chain, P. falciparum Malaria, and the Ebola Filovirus",
volume = "54",
number = "5",
pages = "1157-1169",
doi = "10.1021/jm100938u"
}
Opsenica, I., Burnett, J. C., Gussio, R., Opsenica, D., Todorović, N., Lanteri, C. A., Sciotti, R. J., Gettayacamin, M., Basilico, N., Taramelli, D., Nuss, J. E., Wanner, L., Panchal, R. G., Šolaja, B.,& Bavari, S.. (2011). A Chemotype That Inhibits Three Unrelated Pathogenic Targets: The Botulinum Neurotoxin Serotype A Light Chain, P. falciparum Malaria, and the Ebola Filovirus. in Journal of Medicinal Chemistry
American Chemical Society (ACS)., 54(5), 1157-1169.
https://doi.org/10.1021/jm100938u
Opsenica I, Burnett JC, Gussio R, Opsenica D, Todorović N, Lanteri CA, Sciotti RJ, Gettayacamin M, Basilico N, Taramelli D, Nuss JE, Wanner L, Panchal RG, Šolaja B, Bavari S. A Chemotype That Inhibits Three Unrelated Pathogenic Targets: The Botulinum Neurotoxin Serotype A Light Chain, P. falciparum Malaria, and the Ebola Filovirus. in Journal of Medicinal Chemistry. 2011;54(5):1157-1169.
doi:10.1021/jm100938u .
Opsenica, Igor, Burnett, James C., Gussio, Rick, Opsenica, Dejan, Todorović, Nina, Lanteri, Charlotte A., Sciotti, Richard J., Gettayacamin, Montip, Basilico, Nicoletta, Taramelli, Donatella, Nuss, Jonathan E., Wanner, Laura, Panchal, Rekha G., Šolaja, Bogdan, Bavari, Sina, "A Chemotype That Inhibits Three Unrelated Pathogenic Targets: The Botulinum Neurotoxin Serotype A Light Chain, P. falciparum Malaria, and the Ebola Filovirus" in Journal of Medicinal Chemistry, 54, no. 5 (2011):1157-1169,
https://doi.org/10.1021/jm100938u . .
13
41
42
49

Ribofuranose as a carrier of tetraoxane and 4-aminoquinoline antimalarial pharmacophores

Opsenica, Igor; Smith, Kirsten K.; Gerena, Lucia; Gaica, Sandra; Šolaja, Bogdan

(Belgrade : Serbian Chemical Society, 2008)

TY  - JOUR
AU  - Opsenica, Igor
AU  - Smith, Kirsten K.
AU  - Gerena, Lucia
AU  - Gaica, Sandra
AU  - Šolaja, Bogdan
PY  - 2008
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/7535
AB  - Several tetraoxane and 4-aminoquinoline molecules were prepared in
order to examine the influence of ribofuranose as a carrier molecule on the antimalarial
activity of test compounds. The synthesized compounds showed pronounced
antimalarial activity against Plasmodium falciparum chloroquine susceptible
D6, chloroquine resistant W2 and multidrug-resistant TM91C235 (Thailand)
strains. The aminoquinoline derivative 4 was more active against W2 and
TM91C235 strains than the control compounds (CQ and MFQ).
AB  - U ovom radu prikazana je sinteza nekoliko ribofuranozidnih tetraoksana i 4-aminohinolina u cilju sagledavanja odnosa struktura-aktivnost ove vrste antimalarika. Jedinjenja su pokazala izraženu antimalarijsku aktivnost prema hlorokin-osetljivom (D6), hlorokin-rezistentnom (W2) i višestruko rezistentnom (TM91C235 (Thailand)) soju Plasmodium falciparum. Aminohinolinski derivat 4 je aktivniji prema W2 i TM91C235 sojevima od kontrolnih jedinjenja (hlorokin i meflokin).
PB  - Belgrade : Serbian Chemical Society
T2  - Journal of Serbian Chemical Society
T1  - Ribofuranose as a carrier of tetraoxane and 4-aminoquinoline antimalarial pharmacophores
T1  - Ribofuranoza kao nosač tetraoksanske i 4-aminohinolinske antimalarijske farmakofore
VL  - 73
IS  - 11
SP  - 1021
EP  - 1025
DO  - 10.2298/JSC0811021О
ER  - 
@article{
author = "Opsenica, Igor and Smith, Kirsten K. and Gerena, Lucia and Gaica, Sandra and Šolaja, Bogdan",
year = "2008",
abstract = "Several tetraoxane and 4-aminoquinoline molecules were prepared in
order to examine the influence of ribofuranose as a carrier molecule on the antimalarial
activity of test compounds. The synthesized compounds showed pronounced
antimalarial activity against Plasmodium falciparum chloroquine susceptible
D6, chloroquine resistant W2 and multidrug-resistant TM91C235 (Thailand)
strains. The aminoquinoline derivative 4 was more active against W2 and
TM91C235 strains than the control compounds (CQ and MFQ)., U ovom radu prikazana je sinteza nekoliko ribofuranozidnih tetraoksana i 4-aminohinolina u cilju sagledavanja odnosa struktura-aktivnost ove vrste antimalarika. Jedinjenja su pokazala izraženu antimalarijsku aktivnost prema hlorokin-osetljivom (D6), hlorokin-rezistentnom (W2) i višestruko rezistentnom (TM91C235 (Thailand)) soju Plasmodium falciparum. Aminohinolinski derivat 4 je aktivniji prema W2 i TM91C235 sojevima od kontrolnih jedinjenja (hlorokin i meflokin).",
publisher = "Belgrade : Serbian Chemical Society",
journal = "Journal of Serbian Chemical Society",
title = "Ribofuranose as a carrier of tetraoxane and 4-aminoquinoline antimalarial pharmacophores, Ribofuranoza kao nosač tetraoksanske i 4-aminohinolinske antimalarijske farmakofore",
volume = "73",
number = "11",
pages = "1021-1025",
doi = "10.2298/JSC0811021О"
}
Opsenica, I., Smith, K. K., Gerena, L., Gaica, S.,& Šolaja, B.. (2008). Ribofuranose as a carrier of tetraoxane and 4-aminoquinoline antimalarial pharmacophores. in Journal of Serbian Chemical Society
Belgrade : Serbian Chemical Society., 73(11), 1021-1025.
https://doi.org/10.2298/JSC0811021О
Opsenica I, Smith KK, Gerena L, Gaica S, Šolaja B. Ribofuranose as a carrier of tetraoxane and 4-aminoquinoline antimalarial pharmacophores. in Journal of Serbian Chemical Society. 2008;73(11):1021-1025.
doi:10.2298/JSC0811021О .
Opsenica, Igor, Smith, Kirsten K., Gerena, Lucia, Gaica, Sandra, Šolaja, Bogdan, "Ribofuranose as a carrier of tetraoxane and 4-aminoquinoline antimalarial pharmacophores" in Journal of Serbian Chemical Society, 73, no. 11 (2008):1021-1025,
https://doi.org/10.2298/JSC0811021О . .
2
2

Photolysis of Steroidal 20-Aryl-Substituted 11-Nitrites

Kalvoda, Jaroslav; Grob, Jüren; Bjelaković, Mira; Lorenc, Ljubinka; Mihailović, Milhailo Lj.

(Wiley, 1997)

TY  - JOUR
AU  - Kalvoda, Jaroslav
AU  - Grob, Jüren
AU  - Bjelaković, Mira
AU  - Lorenc, Ljubinka
AU  - Mihailović, Milhailo Lj.
PY  - 1997
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/4188
AB  - The two structurally similar 20‐phenyl‐ and 20‐(4‐methoxyphenyl)‐11‐(nitrosooxy)pregnan‐20‐ol derivatives 4 and 7 behave differently under photolytic conditions, the former nitrous acid ester affording, as a main product, the benzo‐fused hexacyclic compound 9, and the latter the 21‐nitro derivative 12. Mechanistic aspects of these transformations are discussed.
PB  - Wiley
T2  - Helvetica Chimica Acta
T1  - Photolysis of Steroidal 20-Aryl-Substituted 11-Nitrites
VL  - 80
IS  - 4
SP  - 1221
EP  - 1228
DO  - 10.1002/hlca.19970800419
ER  - 
@article{
author = "Kalvoda, Jaroslav and Grob, Jüren and Bjelaković, Mira and Lorenc, Ljubinka and Mihailović, Milhailo Lj.",
year = "1997",
abstract = "The two structurally similar 20‐phenyl‐ and 20‐(4‐methoxyphenyl)‐11‐(nitrosooxy)pregnan‐20‐ol derivatives 4 and 7 behave differently under photolytic conditions, the former nitrous acid ester affording, as a main product, the benzo‐fused hexacyclic compound 9, and the latter the 21‐nitro derivative 12. Mechanistic aspects of these transformations are discussed.",
publisher = "Wiley",
journal = "Helvetica Chimica Acta",
title = "Photolysis of Steroidal 20-Aryl-Substituted 11-Nitrites",
volume = "80",
number = "4",
pages = "1221-1228",
doi = "10.1002/hlca.19970800419"
}
Kalvoda, J., Grob, J., Bjelaković, M., Lorenc, L.,& Mihailović, M. Lj.. (1997). Photolysis of Steroidal 20-Aryl-Substituted 11-Nitrites. in Helvetica Chimica Acta
Wiley., 80(4), 1221-1228.
https://doi.org/10.1002/hlca.19970800419
Kalvoda J, Grob J, Bjelaković M, Lorenc L, Mihailović ML. Photolysis of Steroidal 20-Aryl-Substituted 11-Nitrites. in Helvetica Chimica Acta. 1997;80(4):1221-1228.
doi:10.1002/hlca.19970800419 .
Kalvoda, Jaroslav, Grob, Jüren, Bjelaković, Mira, Lorenc, Ljubinka, Mihailović, Milhailo Lj., "Photolysis of Steroidal 20-Aryl-Substituted 11-Nitrites" in Helvetica Chimica Acta, 80, no. 4 (1997):1221-1228,
https://doi.org/10.1002/hlca.19970800419 . .
3
2
2

Photochemically induced mercuric oxide - iodine oxidation of some unsaturated steroid compounds

Dabović, Milan; Bjelaković, Mira; Andrejević, V.; Lorenc, Ljubinka; Mihailović, Milhailo Lj.

(Pergamon, 1994)

TY  - JOUR
AU  - Dabović, Milan
AU  - Bjelaković, Mira
AU  - Andrejević, V.
AU  - Lorenc, Ljubinka
AU  - Mihailović, Milhailo Lj.
PY  - 1994
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/2697
AB  - Photochemically induced HgO/I2 oxidation of cholest-5-en-3α-ol (6) and cholest-5-en-3β-ol (7) afforded (Scheme 3) products arising from the corresponding alkoxy radicals (12, 13 and 14a,b) and from attack of the I2O intermediate at the olefinic double bond (epoxides 15a and 16a,b respectively). With cholest-5-ene-1α,3β-diol 3-acetate (8) and cholest-7-ene-3β,5α-diol 3-acetate (9) the HgO/I2 oxidation led to unresolvable complex mixtures (Scheme 5). With the same reagent cholest-5-en-3α-ol acetate (10) and cholest-5-en-3β-ol acetate (11) underwent exclusively attack by I2O, to give epoxides 20a,b, iodohydrin 21, and rearranged products 19 and 22 (Scheme 7), in the case of 10, and predominantly epoxides 23a,b (Scheme 8), in the case of 11. © 1994.
PB  - Pergamon
T2  - Tetrahedron
T1  - Photochemically induced mercuric oxide - iodine oxidation of some unsaturated steroid compounds
VL  - 50
IS  - 6
SP  - 1833
EP  - 1846
DO  - 10.1016/S0040-4020(01)80855-3
ER  - 
@article{
author = "Dabović, Milan and Bjelaković, Mira and Andrejević, V. and Lorenc, Ljubinka and Mihailović, Milhailo Lj.",
year = "1994",
abstract = "Photochemically induced HgO/I2 oxidation of cholest-5-en-3α-ol (6) and cholest-5-en-3β-ol (7) afforded (Scheme 3) products arising from the corresponding alkoxy radicals (12, 13 and 14a,b) and from attack of the I2O intermediate at the olefinic double bond (epoxides 15a and 16a,b respectively). With cholest-5-ene-1α,3β-diol 3-acetate (8) and cholest-7-ene-3β,5α-diol 3-acetate (9) the HgO/I2 oxidation led to unresolvable complex mixtures (Scheme 5). With the same reagent cholest-5-en-3α-ol acetate (10) and cholest-5-en-3β-ol acetate (11) underwent exclusively attack by I2O, to give epoxides 20a,b, iodohydrin 21, and rearranged products 19 and 22 (Scheme 7), in the case of 10, and predominantly epoxides 23a,b (Scheme 8), in the case of 11. © 1994.",
publisher = "Pergamon",
journal = "Tetrahedron",
title = "Photochemically induced mercuric oxide - iodine oxidation of some unsaturated steroid compounds",
volume = "50",
number = "6",
pages = "1833-1846",
doi = "10.1016/S0040-4020(01)80855-3"
}
Dabović, M., Bjelaković, M., Andrejević, V., Lorenc, L.,& Mihailović, M. Lj.. (1994). Photochemically induced mercuric oxide - iodine oxidation of some unsaturated steroid compounds. in Tetrahedron
Pergamon., 50(6), 1833-1846.
https://doi.org/10.1016/S0040-4020(01)80855-3
Dabović M, Bjelaković M, Andrejević V, Lorenc L, Mihailović ML. Photochemically induced mercuric oxide - iodine oxidation of some unsaturated steroid compounds. in Tetrahedron. 1994;50(6):1833-1846.
doi:10.1016/S0040-4020(01)80855-3 .
Dabović, Milan, Bjelaković, Mira, Andrejević, V., Lorenc, Ljubinka, Mihailović, Milhailo Lj., "Photochemically induced mercuric oxide - iodine oxidation of some unsaturated steroid compounds" in Tetrahedron, 50, no. 6 (1994):1833-1846,
https://doi.org/10.1016/S0040-4020(01)80855-3 . .
4
5

Crystal Structure and Solid State Conformation of 5‐Hydroxy‐8,9‐Dioxo‐8,9‐Seco‐α‐Cholestan‐3β‐yl Acetate

Tinant, Bernard; Declercq, J P; Dabović, Milan; Krstić, Natalija; Lorenc, Ljubinka; Mihailović, Milhailo Lj.

(Comltb van Beheer van het Bulletin V.Z.W., 1993)

TY  - JOUR
AU  - Tinant, Bernard
AU  - Declercq, J P
AU  - Dabović, Milan
AU  - Krstić, Natalija
AU  - Lorenc, Ljubinka
AU  - Mihailović, Milhailo Lj.
PY  - 1993
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/2704
AB  - The molecular structure of the title compound, which might be a possible intermediate in the synthesis of 5,10:8,9‐diseco‐steroids (=steroklastanes), was determined by X‐ray analysis. Hydrogen bonding between the 5α‐hydroxyl group and the 9‐oxo function attached to the ten‐membered ring, and the presence of two conformational forms of the side‐chain in the solid state structure of 2 are established. Copyright © 1993 Wiley‐VCH Verlag GmbH & Co. KGaA, Weinheim
PB  - Comltb van Beheer van het Bulletin V.Z.W.
T2  - Bulletin des Sociétés Chimiques Belges
T1  - Crystal Structure and Solid State Conformation of 5‐Hydroxy‐8,9‐Dioxo‐8,9‐Seco‐α‐Cholestan‐3β‐yl Acetate
VL  - 102
IS  - 8
SP  - 539
EP  - 544
DO  - 10.1002/bscb.19931020806
ER  - 
@article{
author = "Tinant, Bernard and Declercq, J P and Dabović, Milan and Krstić, Natalija and Lorenc, Ljubinka and Mihailović, Milhailo Lj.",
year = "1993",
abstract = "The molecular structure of the title compound, which might be a possible intermediate in the synthesis of 5,10:8,9‐diseco‐steroids (=steroklastanes), was determined by X‐ray analysis. Hydrogen bonding between the 5α‐hydroxyl group and the 9‐oxo function attached to the ten‐membered ring, and the presence of two conformational forms of the side‐chain in the solid state structure of 2 are established. Copyright © 1993 Wiley‐VCH Verlag GmbH & Co. KGaA, Weinheim",
publisher = "Comltb van Beheer van het Bulletin V.Z.W.",
journal = "Bulletin des Sociétés Chimiques Belges",
title = "Crystal Structure and Solid State Conformation of 5‐Hydroxy‐8,9‐Dioxo‐8,9‐Seco‐α‐Cholestan‐3β‐yl Acetate",
volume = "102",
number = "8",
pages = "539-544",
doi = "10.1002/bscb.19931020806"
}
Tinant, B., Declercq, J. P., Dabović, M., Krstić, N., Lorenc, L.,& Mihailović, M. Lj.. (1993). Crystal Structure and Solid State Conformation of 5‐Hydroxy‐8,9‐Dioxo‐8,9‐Seco‐α‐Cholestan‐3β‐yl Acetate. in Bulletin des Sociétés Chimiques Belges
Comltb van Beheer van het Bulletin V.Z.W.., 102(8), 539-544.
https://doi.org/10.1002/bscb.19931020806
Tinant B, Declercq JP, Dabović M, Krstić N, Lorenc L, Mihailović ML. Crystal Structure and Solid State Conformation of 5‐Hydroxy‐8,9‐Dioxo‐8,9‐Seco‐α‐Cholestan‐3β‐yl Acetate. in Bulletin des Sociétés Chimiques Belges. 1993;102(8):539-544.
doi:10.1002/bscb.19931020806 .
Tinant, Bernard, Declercq, J P, Dabović, Milan, Krstić, Natalija, Lorenc, Ljubinka, Mihailović, Milhailo Lj., "Crystal Structure and Solid State Conformation of 5‐Hydroxy‐8,9‐Dioxo‐8,9‐Seco‐α‐Cholestan‐3β‐yl Acetate" in Bulletin des Sociétés Chimiques Belges, 102, no. 8 (1993):539-544,
https://doi.org/10.1002/bscb.19931020806 . .
1
1

Non-sensitized photooxygenation of some steroidal isoxazolidines

Lorenc, Ljubinka; Juranić, Ivan; Dabović, Milan; Mihailović, Milhailo Lj.

(Pergamon press, 1991)

TY  - JOUR
AU  - Lorenc, Ljubinka
AU  - Juranić, Ivan
AU  - Dabović, Milan
AU  - Mihailović, Milhailo Lj.
PY  - 1991
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/2698
AB  - UV irradiation of the steroidal isoxazolidines 2a, 2b, and 2c in various solvents in the presence of molecular oxygen, results in oxidative cleavage of the epoxyimino bridge to give several products; the N-unsubstituted isoxazolidine 2a afforded the nitro products 3, 4, and 5 and the azoxy compounds 6 and 7, while the N-methyl and N-acetyl derivatives 2b and 2c produced only the nitro compounds 3 and 5 as sole identifiable material. An explanation of the observed photooxygenation processes involving exciplex formation followed by proton transfer from isaxazolidine to molecular oxygen is presented. © 1991.
PB  - Pergamon press
T2  - Tetrahedron
T1  - Non-sensitized photooxygenation of some steroidal isoxazolidines
VL  - 47
IS  - 32
SP  - 6389
EP  - 6398
DO  - 10.1016/S0040-4020(01)86567-4
ER  - 
@article{
author = "Lorenc, Ljubinka and Juranić, Ivan and Dabović, Milan and Mihailović, Milhailo Lj.",
year = "1991",
abstract = "UV irradiation of the steroidal isoxazolidines 2a, 2b, and 2c in various solvents in the presence of molecular oxygen, results in oxidative cleavage of the epoxyimino bridge to give several products; the N-unsubstituted isoxazolidine 2a afforded the nitro products 3, 4, and 5 and the azoxy compounds 6 and 7, while the N-methyl and N-acetyl derivatives 2b and 2c produced only the nitro compounds 3 and 5 as sole identifiable material. An explanation of the observed photooxygenation processes involving exciplex formation followed by proton transfer from isaxazolidine to molecular oxygen is presented. © 1991.",
publisher = "Pergamon press",
journal = "Tetrahedron",
title = "Non-sensitized photooxygenation of some steroidal isoxazolidines",
volume = "47",
number = "32",
pages = "6389-6398",
doi = "10.1016/S0040-4020(01)86567-4"
}
Lorenc, L., Juranić, I., Dabović, M.,& Mihailović, M. Lj.. (1991). Non-sensitized photooxygenation of some steroidal isoxazolidines. in Tetrahedron
Pergamon press., 47(32), 6389-6398.
https://doi.org/10.1016/S0040-4020(01)86567-4
Lorenc L, Juranić I, Dabović M, Mihailović ML. Non-sensitized photooxygenation of some steroidal isoxazolidines. in Tetrahedron. 1991;47(32):6389-6398.
doi:10.1016/S0040-4020(01)86567-4 .
Lorenc, Ljubinka, Juranić, Ivan, Dabović, Milan, Mihailović, Milhailo Lj., "Non-sensitized photooxygenation of some steroidal isoxazolidines" in Tetrahedron, 47, no. 32 (1991):6389-6398,
https://doi.org/10.1016/S0040-4020(01)86567-4 . .
4
5

Free-radical oxidative transformations of androst-4-ene-3β,9α,17β-triol 3,17-diacetate

Mihailović, Milhailo Lj.; Lorenc, Ljubinka; Dabović, Milan; Bjelaković, Mira

(1988)

TY  - JOUR
AU  - Mihailović, Milhailo Lj.
AU  - Lorenc, Ljubinka
AU  - Dabović, Milan
AU  - Bjelaković, Mira
PY  - 1988
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/2699
AB  - The oxidation of androst-4-ene-3β,9α,17β-triol 3,17-diacetate (2) with lead tetraacetate resulted mainly In β-fragmentation of the C(9)-C(10) bond to give a mixture of 10α- and 10β-acetoxy-Δ4-unsaturated 9,10-seco-steroidal ketones (3a and 3b) as the minor components (in ~7% yield) and the rearranged 4β-acetoxy-Δ5(10) -unsaturated 9,10-seco-9-ketone (4) as the major product (in 61% yield). Unexpectedly, when the same substrate (2) was subjected to the mercuric oxide - iodine oxidation, it underwent predominantly α-epoxidation of the olefinic double bond to produce the 4α,5α-epoxy derivative (5) (in 58% yield). © 1988.
T2  - Tetrahedron
T1  - Free-radical oxidative transformations of androst-4-ene-3β,9α,17β-triol 3,17-diacetate
VL  - 44
IS  - 19
SP  - 6201
EP  - 6206
DO  - 10.1016/S0040-4020(01)89810-0
ER  - 
@article{
author = "Mihailović, Milhailo Lj. and Lorenc, Ljubinka and Dabović, Milan and Bjelaković, Mira",
year = "1988",
abstract = "The oxidation of androst-4-ene-3β,9α,17β-triol 3,17-diacetate (2) with lead tetraacetate resulted mainly In β-fragmentation of the C(9)-C(10) bond to give a mixture of 10α- and 10β-acetoxy-Δ4-unsaturated 9,10-seco-steroidal ketones (3a and 3b) as the minor components (in ~7% yield) and the rearranged 4β-acetoxy-Δ5(10) -unsaturated 9,10-seco-9-ketone (4) as the major product (in 61% yield). Unexpectedly, when the same substrate (2) was subjected to the mercuric oxide - iodine oxidation, it underwent predominantly α-epoxidation of the olefinic double bond to produce the 4α,5α-epoxy derivative (5) (in 58% yield). © 1988.",
journal = "Tetrahedron",
title = "Free-radical oxidative transformations of androst-4-ene-3β,9α,17β-triol 3,17-diacetate",
volume = "44",
number = "19",
pages = "6201-6206",
doi = "10.1016/S0040-4020(01)89810-0"
}
Mihailović, M. Lj., Lorenc, L., Dabović, M.,& Bjelaković, M.. (1988). Free-radical oxidative transformations of androst-4-ene-3β,9α,17β-triol 3,17-diacetate. in Tetrahedron, 44(19), 6201-6206.
https://doi.org/10.1016/S0040-4020(01)89810-0
Mihailović ML, Lorenc L, Dabović M, Bjelaković M. Free-radical oxidative transformations of androst-4-ene-3β,9α,17β-triol 3,17-diacetate. in Tetrahedron. 1988;44(19):6201-6206.
doi:10.1016/S0040-4020(01)89810-0 .
Mihailović, Milhailo Lj., Lorenc, Ljubinka, Dabović, Milan, Bjelaković, Mira, "Free-radical oxidative transformations of androst-4-ene-3β,9α,17β-triol 3,17-diacetate" in Tetrahedron, 44, no. 19 (1988):6201-6206,
https://doi.org/10.1016/S0040-4020(01)89810-0 . .
5
4

Circular dichroism of some cyclopropane ring containing 1,3-cyclo-5,10-seco-steroidal ketones

Lorenc, Ljubinka; Dabović, Milan; Juranić, Ivan; Mihailović, Milhailo Lj.; Snatzke, G; Tóth, G

(Elsevier, 1982)

TY  - JOUR
AU  - Lorenc, Ljubinka
AU  - Dabović, Milan
AU  - Juranić, Ivan
AU  - Mihailović, Milhailo Lj.
AU  - Snatzke, G
AU  - Tóth, G
PY  - 1982
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/2696
AB  - Circular dichroism of the rearranged keto steroids 3 and 4, containing a condensed three and nine-membered ring system, shows that the conformation of the nine-membered ring is the same in solution as in the crystal; reduction of the kto group does not change this situation. CD also indicates that epimerization at C(5) in the pair 7 8 and the pair 11 12 leaves the cyclononanone ring conformation unchanged. © 1982.
PB  - Elsevier
T2  - Tetrahedron
T1  - Circular dichroism of some cyclopropane ring containing 1,3-cyclo-5,10-seco-steroidal ketones
VL  - 38
IS  - 21
SP  - 3163
EP  - 3168
DO  - 10.1016/0040-4020(82)80053-7
ER  - 
@article{
author = "Lorenc, Ljubinka and Dabović, Milan and Juranić, Ivan and Mihailović, Milhailo Lj. and Snatzke, G and Tóth, G",
year = "1982",
abstract = "Circular dichroism of the rearranged keto steroids 3 and 4, containing a condensed three and nine-membered ring system, shows that the conformation of the nine-membered ring is the same in solution as in the crystal; reduction of the kto group does not change this situation. CD also indicates that epimerization at C(5) in the pair 7 8 and the pair 11 12 leaves the cyclononanone ring conformation unchanged. © 1982.",
publisher = "Elsevier",
journal = "Tetrahedron",
title = "Circular dichroism of some cyclopropane ring containing 1,3-cyclo-5,10-seco-steroidal ketones",
volume = "38",
number = "21",
pages = "3163-3168",
doi = "10.1016/0040-4020(82)80053-7"
}
Lorenc, L., Dabović, M., Juranić, I., Mihailović, M. Lj., Snatzke, G.,& Tóth, G.. (1982). Circular dichroism of some cyclopropane ring containing 1,3-cyclo-5,10-seco-steroidal ketones. in Tetrahedron
Elsevier., 38(21), 3163-3168.
https://doi.org/10.1016/0040-4020(82)80053-7
Lorenc L, Dabović M, Juranić I, Mihailović ML, Snatzke G, Tóth G. Circular dichroism of some cyclopropane ring containing 1,3-cyclo-5,10-seco-steroidal ketones. in Tetrahedron. 1982;38(21):3163-3168.
doi:10.1016/0040-4020(82)80053-7 .
Lorenc, Ljubinka, Dabović, Milan, Juranić, Ivan, Mihailović, Milhailo Lj., Snatzke, G, Tóth, G, "Circular dichroism of some cyclopropane ring containing 1,3-cyclo-5,10-seco-steroidal ketones" in Tetrahedron, 38, no. 21 (1982):3163-3168,
https://doi.org/10.1016/0040-4020(82)80053-7 . .
1
1

Synthesis, structure, and reactions of secosteroids containing a medium-sized ring. Part 17. Structure-reactivity relationship in the solvolysis of 5,10-secosteroidal 3-tosylates

Lorenc, Ljubinka; Gašić, Miroslav J.; Juranić, Ivan; Dabović, Milan; Minailović, M. Lj.

(Royal Society of Chemistry, 1980)

TY  - JOUR
AU  - Lorenc, Ljubinka
AU  - Gašić, Miroslav J.
AU  - Juranić, Ivan
AU  - Dabović, Milan
AU  - Minailović, M. Lj.
PY  - 1980
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/2709
AB  - Kinetic measurements of the solvolysis of (Z)-3α- and (Z)-3β-, and (E)-3α- and (E)-3β-tosyloxy-5,10-secocholest-1(10)-en-5-ones in buffered aqueous acetone (90 : 10 v/v) reveal that the (Z)-3α-, (E)-3α-, and (E)-3β-tosylates are solvolysed according to a first-order rate law (the relative rates being ca. 1 : 3 : 8), while the (Z)-3β-ester, under the same conditions, reacts at a much slower rate by a complex mechanism, the kinetics of which are best approximated by a second-order law. These data and product analysis indicate that the former three esters are solvolysed with considerable double bond participation [resulting in the case of the (E)-3-esters in intramolecular cyclopropane ring closure], and that this interaction is unimportant for the (Z)-3β-tosylate. On the basis of conformational analysis of the starting tosylates and stereoelectronic requirements for homoallylic interaction, a possible mechanistic pathway for these solvolyses is proposed.
PB  - Royal Society of Chemistry
T2  - Journal of the Chemical Society, Perkin Transactions 2
T1  - Synthesis, structure, and reactions of secosteroids containing a medium-sized ring. Part 17. Structure-reactivity relationship in the solvolysis of 5,10-secosteroidal 3-tosylates
IS  - 9
SP  - 1356
EP  - 1365
UR  - https://hdl.handle.net/21.15107/rcub_cer_2709
ER  - 
@article{
author = "Lorenc, Ljubinka and Gašić, Miroslav J. and Juranić, Ivan and Dabović, Milan and Minailović, M. Lj.",
year = "1980",
abstract = "Kinetic measurements of the solvolysis of (Z)-3α- and (Z)-3β-, and (E)-3α- and (E)-3β-tosyloxy-5,10-secocholest-1(10)-en-5-ones in buffered aqueous acetone (90 : 10 v/v) reveal that the (Z)-3α-, (E)-3α-, and (E)-3β-tosylates are solvolysed according to a first-order rate law (the relative rates being ca. 1 : 3 : 8), while the (Z)-3β-ester, under the same conditions, reacts at a much slower rate by a complex mechanism, the kinetics of which are best approximated by a second-order law. These data and product analysis indicate that the former three esters are solvolysed with considerable double bond participation [resulting in the case of the (E)-3-esters in intramolecular cyclopropane ring closure], and that this interaction is unimportant for the (Z)-3β-tosylate. On the basis of conformational analysis of the starting tosylates and stereoelectronic requirements for homoallylic interaction, a possible mechanistic pathway for these solvolyses is proposed.",
publisher = "Royal Society of Chemistry",
journal = "Journal of the Chemical Society, Perkin Transactions 2",
title = "Synthesis, structure, and reactions of secosteroids containing a medium-sized ring. Part 17. Structure-reactivity relationship in the solvolysis of 5,10-secosteroidal 3-tosylates",
number = "9",
pages = "1356-1365",
url = "https://hdl.handle.net/21.15107/rcub_cer_2709"
}
Lorenc, L., Gašić, M. J., Juranić, I., Dabović, M.,& Minailović, M. Lj.. (1980). Synthesis, structure, and reactions of secosteroids containing a medium-sized ring. Part 17. Structure-reactivity relationship in the solvolysis of 5,10-secosteroidal 3-tosylates. in Journal of the Chemical Society, Perkin Transactions 2
Royal Society of Chemistry.(9), 1356-1365.
https://hdl.handle.net/21.15107/rcub_cer_2709
Lorenc L, Gašić MJ, Juranić I, Dabović M, Minailović ML. Synthesis, structure, and reactions of secosteroids containing a medium-sized ring. Part 17. Structure-reactivity relationship in the solvolysis of 5,10-secosteroidal 3-tosylates. in Journal of the Chemical Society, Perkin Transactions 2. 1980;(9):1356-1365.
https://hdl.handle.net/21.15107/rcub_cer_2709 .
Lorenc, Ljubinka, Gašić, Miroslav J., Juranić, Ivan, Dabović, Milan, Minailović, M. Lj., "Synthesis, structure, and reactions of secosteroids containing a medium-sized ring. Part 17. Structure-reactivity relationship in the solvolysis of 5,10-secosteroidal 3-tosylates" in Journal of the Chemical Society, Perkin Transactions 2, no. 9 (1980):1356-1365,
https://hdl.handle.net/21.15107/rcub_cer_2709 .
4

X-ray and carbon-13 nuclear magnetic resonance characterization of cyclopropane derivatives obtained by solvolysis of (E)-3α- and (E)-3β-hydroxy-5,10-seco-1(10)-cholesten-5-one tosylates

Mihailović, Milhailo Lj.; Lorenc, Ljubinka; Dabović, Milan; Juranić, Ivan; Wenkert, E.; Bernassau, J.-M.; Raju, M S; McPhail, A T; Miller, R W

(Pergamon Press, 1979)

TY  - JOUR
AU  - Mihailović, Milhailo Lj.
AU  - Lorenc, Ljubinka
AU  - Dabović, Milan
AU  - Juranić, Ivan
AU  - Wenkert, E.
AU  - Bernassau, J.-M.
AU  - Raju, M S
AU  - McPhail, A T
AU  - Miller, R W
PY  - 1979
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/2703
AB  - The stereochemistries and conformations of the cyclopropane ring containing compounds derived from (E-3α- and (E)-3β-hydroxy-5,10-seco-1(10)-cholesten-5-one tosylates have been determined by X-ray methods and the results correlated with 13C nmr chemical shift data. © 1979.
PB  - Pergamon Press
T2  - Tetrahedron Letters
T1  - X-ray and carbon-13 nuclear magnetic resonance characterization of cyclopropane derivatives obtained by solvolysis of (E)-3α- and (E)-3β-hydroxy-5,10-seco-1(10)-cholesten-5-one tosylates
VL  - 20
IS  - 51
SP  - 4917
EP  - 4920
DO  - 10.1016/S0040-4039(01)86749-6
ER  - 
@article{
author = "Mihailović, Milhailo Lj. and Lorenc, Ljubinka and Dabović, Milan and Juranić, Ivan and Wenkert, E. and Bernassau, J.-M. and Raju, M S and McPhail, A T and Miller, R W",
year = "1979",
abstract = "The stereochemistries and conformations of the cyclopropane ring containing compounds derived from (E-3α- and (E)-3β-hydroxy-5,10-seco-1(10)-cholesten-5-one tosylates have been determined by X-ray methods and the results correlated with 13C nmr chemical shift data. © 1979.",
publisher = "Pergamon Press",
journal = "Tetrahedron Letters",
title = "X-ray and carbon-13 nuclear magnetic resonance characterization of cyclopropane derivatives obtained by solvolysis of (E)-3α- and (E)-3β-hydroxy-5,10-seco-1(10)-cholesten-5-one tosylates",
volume = "20",
number = "51",
pages = "4917-4920",
doi = "10.1016/S0040-4039(01)86749-6"
}
Mihailović, M. Lj., Lorenc, L., Dabović, M., Juranić, I., Wenkert, E., Bernassau, J.-M., Raju, M. S., McPhail, A. T.,& Miller, R. W.. (1979). X-ray and carbon-13 nuclear magnetic resonance characterization of cyclopropane derivatives obtained by solvolysis of (E)-3α- and (E)-3β-hydroxy-5,10-seco-1(10)-cholesten-5-one tosylates. in Tetrahedron Letters
Pergamon Press., 20(51), 4917-4920.
https://doi.org/10.1016/S0040-4039(01)86749-6
Mihailović ML, Lorenc L, Dabović M, Juranić I, Wenkert E, Bernassau J, Raju MS, McPhail AT, Miller RW. X-ray and carbon-13 nuclear magnetic resonance characterization of cyclopropane derivatives obtained by solvolysis of (E)-3α- and (E)-3β-hydroxy-5,10-seco-1(10)-cholesten-5-one tosylates. in Tetrahedron Letters. 1979;20(51):4917-4920.
doi:10.1016/S0040-4039(01)86749-6 .
Mihailović, Milhailo Lj., Lorenc, Ljubinka, Dabović, Milan, Juranić, Ivan, Wenkert, E., Bernassau, J.-M., Raju, M S, McPhail, A T, Miller, R W, "X-ray and carbon-13 nuclear magnetic resonance characterization of cyclopropane derivatives obtained by solvolysis of (E)-3α- and (E)-3β-hydroxy-5,10-seco-1(10)-cholesten-5-one tosylates" in Tetrahedron Letters, 20, no. 51 (1979):4917-4920,
https://doi.org/10.1016/S0040-4039(01)86749-6 . .
1
4

Oxygen reduction of electrode surfaces modified by foreign metal adatoms

Adžić, Radoslav R.; Tripković, Amalija; Atanasoski, Radoslav

(Elsevier, 1978)

TY  - JOUR
AU  - Adžić, Radoslav R.
AU  - Tripković, Amalija
AU  - Atanasoski, Radoslav
PY  - 1978
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/2756
PB  - Elsevier
T2  - Journal of Electroanalytical Chemistry
T2  - Journal of Electroanalytical Chemistry
T1  - Oxygen reduction of electrode surfaces modified by foreign metal adatoms
VL  - 94
IS  - 3
SP  - 231
EP  - 235
DO  - 10.1016/S0022-0728(78)80318-0
ER  - 
@article{
author = "Adžić, Radoslav R. and Tripković, Amalija and Atanasoski, Radoslav",
year = "1978",
publisher = "Elsevier",
journal = "Journal of Electroanalytical Chemistry, Journal of Electroanalytical Chemistry",
title = "Oxygen reduction of electrode surfaces modified by foreign metal adatoms",
volume = "94",
number = "3",
pages = "231-235",
doi = "10.1016/S0022-0728(78)80318-0"
}
Adžić, R. R., Tripković, A.,& Atanasoski, R.. (1978). Oxygen reduction of electrode surfaces modified by foreign metal adatoms. in Journal of Electroanalytical Chemistry
Elsevier., 94(3), 231-235.
https://doi.org/10.1016/S0022-0728(78)80318-0
Adžić RR, Tripković A, Atanasoski R. Oxygen reduction of electrode surfaces modified by foreign metal adatoms. in Journal of Electroanalytical Chemistry. 1978;94(3):231-235.
doi:10.1016/S0022-0728(78)80318-0 .
Adžić, Radoslav R., Tripković, Amalija, Atanasoski, Radoslav, "Oxygen reduction of electrode surfaces modified by foreign metal adatoms" in Journal of Electroanalytical Chemistry, 94, no. 3 (1978):231-235,
https://doi.org/10.1016/S0022-0728(78)80318-0 . .
49
48