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

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

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

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

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

TY  - JOUR
AU  - Terzić-Jovanović, Nataša
AU  - Opsenica, Dejan
AU  - Milić, Dragana
AU  - Tinant, Bernard
AU  - Smith, K. S.
AU  - Milhous, Wilbur K.
AU  - Šolaja, Bogdan
PY  - 2007
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/350
AB  - The synthesis of deoxycholic acid (DCA)- and cholic acid (CA)-derived mixed tetraoxanes revealed that N-(2-dimethylamino)ethyl derivatives are potent antimalarials in vitro and in vivo. The tetraoxanes presented in this paper are dual inhibitors: besides curing mice in vivo without observed toxic effects, they kill cancer cell lines at very low concentrations. For example, DCA and CA derivatives 16 and 25 cured 3/5 (160 mg/kg/day) and 2/5 (40 mg/kg/day, MTD >960 mg/kg), respectively, and they were extremely active against melanoma LOX IMVI cancer, LC50 = 22 nM and 69 nM, respectively.
PB  - American Chemical Society (ACS)
T2  - Journal of Medicinal Chemistry
T1  - Deoxycholic acid-derived tetraoxane antimalarials and antiproliferatives
VL  - 50
IS  - 21
SP  - 5118
EP  - 5127
DO  - 10.1021/jm070684m
ER  - 

@article{
author = "Terzić-Jovanović, Nataša and Opsenica, Dejan and Milić, Dragana and Tinant, Bernard and Smith, K. S. and Milhous, Wilbur K. and Šolaja, Bogdan",
year = "2007",
abstract = "The synthesis of deoxycholic acid (DCA)- and cholic acid (CA)-derived mixed tetraoxanes revealed that N-(2-dimethylamino)ethyl derivatives are potent antimalarials in vitro and in vivo. The tetraoxanes presented in this paper are dual inhibitors: besides curing mice in vivo without observed toxic effects, they kill cancer cell lines at very low concentrations. For example, DCA and CA derivatives 16 and 25 cured 3/5 (160 mg/kg/day) and 2/5 (40 mg/kg/day, MTD >960 mg/kg), respectively, and they were extremely active against melanoma LOX IMVI cancer, LC50 = 22 nM and 69 nM, respectively.",
publisher = "American Chemical Society (ACS)",
journal = "Journal of Medicinal Chemistry",
title = "Deoxycholic acid-derived tetraoxane antimalarials and antiproliferatives",
volume = "50",
number = "21",
pages = "5118-5127",
doi = "10.1021/jm070684m"
}

Terzić-Jovanović, N., Opsenica, D., Milić, D., Tinant, B., Smith, K. S., Milhous, W. K.,& Šolaja, B.. (2007). Deoxycholic acid-derived tetraoxane antimalarials and antiproliferatives. in Journal of Medicinal Chemistry
American Chemical Society (ACS)., 50(21), 5118-5127.
https://doi.org/10.1021/jm070684m

Terzić-Jovanović N, Opsenica D, Milić D, Tinant B, Smith KS, Milhous WK, Šolaja B. Deoxycholic acid-derived tetraoxane antimalarials and antiproliferatives. in Journal of Medicinal Chemistry. 2007;50(21):5118-5127.
doi:10.1021/jm070684m .

Terzić-Jovanović, Nataša, Opsenica, Dejan, Milić, Dragana, Tinant, Bernard, Smith, K. S., Milhous, Wilbur K., Šolaja, Bogdan, "Deoxycholic acid-derived tetraoxane antimalarials and antiproliferatives" in Journal of Medicinal Chemistry, 50, no. 21 (2007):5118-5127,
https://doi.org/10.1021/jm070684m . .

TY  - JOUR
AU  - Opsenica, Igor
AU  - Terzić-Jovanović, Nataša
AU  - Opsenica, Dejan
AU  - Angelovski, Goran
AU  - Lehnig, Manfred
AU  - Eilbracht, Peter
AU  - Tinant, Bernard
AU  - Juranić, Zorica
AU  - Smith, Kirsten S.
AU  - Yang, Young S.
AU  - Diaz, Damaris S.
AU  - Smith, Philip L.
AU  - Milhous, Wilbur K.
AU  - Đoković, Dejan
AU  - Šolaja, Bogdan
PY  - 2006
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/3096
AB  - Mixed tetraoxanes 5a and 13 synthesized from cholic acid and 4-oxocyclohexanecarboxylic acid were as active as artemisinin against chloroquine-susceptible, chloroquine-resistant, and multidrug-resistant Plasmodium falciparum strains (IC50, IC90). Most active 13 is metabolically stable in in vitro metabolism studies. In vivo studies on tetraoxanes with a C(4'') methyl group afforded compound 15, which cured 4/5 mice at 600 and 200 mg, kg(-1), day(-1), and 2/5 mice at 50 mg, kg(-1), day(-1), showing no toxic effects. Tetraoxane 19 was an extremely active antiproliferative with LC50 of 17 nM and maximum tolerated dose of 400 mg/kg. In Fe(II)-induced scission of tetraoxane antimalarials only RO center dot radicals were detected by EPR experiments. This finding and the indication of Fe(IV)=O species led us to propose that RO center dot radicals are probably capable of inducing the parasite's death. Our results suggest that C radicals are possibly not the only lethal species derived from peroxide prodrug antimalarials, as currently believed.
PB  - American Chemical Society (ACS)
T2  - Journal of Medicinal Chemistry
T1  - Tetraoxane antimalarials and their reaction with Fe(II)
VL  - 49
IS  - 13
SP  - 3790
EP  - 3799
DO  - 10.1021/jm050966r
ER  - 

@article{
author = "Opsenica, Igor and Terzić-Jovanović, Nataša and Opsenica, Dejan and Angelovski, Goran and Lehnig, Manfred and Eilbracht, Peter and Tinant, Bernard and Juranić, Zorica and Smith, Kirsten S. and Yang, Young S. and Diaz, Damaris S. and Smith, Philip L. and Milhous, Wilbur K. and Đoković, Dejan and Šolaja, Bogdan",
year = "2006",
abstract = "Mixed tetraoxanes 5a and 13 synthesized from cholic acid and 4-oxocyclohexanecarboxylic acid were as active as artemisinin against chloroquine-susceptible, chloroquine-resistant, and multidrug-resistant Plasmodium falciparum strains (IC50, IC90). Most active 13 is metabolically stable in in vitro metabolism studies. In vivo studies on tetraoxanes with a C(4'') methyl group afforded compound 15, which cured 4/5 mice at 600 and 200 mg, kg(-1), day(-1), and 2/5 mice at 50 mg, kg(-1), day(-1), showing no toxic effects. Tetraoxane 19 was an extremely active antiproliferative with LC50 of 17 nM and maximum tolerated dose of 400 mg/kg. In Fe(II)-induced scission of tetraoxane antimalarials only RO center dot radicals were detected by EPR experiments. This finding and the indication of Fe(IV)=O species led us to propose that RO center dot radicals are probably capable of inducing the parasite's death. Our results suggest that C radicals are possibly not the only lethal species derived from peroxide prodrug antimalarials, as currently believed.",
publisher = "American Chemical Society (ACS)",
journal = "Journal of Medicinal Chemistry",
title = "Tetraoxane antimalarials and their reaction with Fe(II)",
volume = "49",
number = "13",
pages = "3790-3799",
doi = "10.1021/jm050966r"
}

Opsenica, I., Terzić-Jovanović, N., Opsenica, D., Angelovski, G., Lehnig, M., Eilbracht, P., Tinant, B., Juranić, Z., Smith, K. S., Yang, Y. S., Diaz, D. S., Smith, P. L., Milhous, W. K., Đoković, D.,& Šolaja, B.. (2006). Tetraoxane antimalarials and their reaction with Fe(II). in Journal of Medicinal Chemistry
American Chemical Society (ACS)., 49(13), 3790-3799.
https://doi.org/10.1021/jm050966r

Opsenica I, Terzić-Jovanović N, Opsenica D, Angelovski G, Lehnig M, Eilbracht P, Tinant B, Juranić Z, Smith KS, Yang YS, Diaz DS, Smith PL, Milhous WK, Đoković D, Šolaja B. Tetraoxane antimalarials and their reaction with Fe(II). in Journal of Medicinal Chemistry. 2006;49(13):3790-3799.
doi:10.1021/jm050966r .

Opsenica, Igor, Terzić-Jovanović, Nataša, Opsenica, Dejan, Angelovski, Goran, Lehnig, Manfred, Eilbracht, Peter, Tinant, Bernard, Juranić, Zorica, Smith, Kirsten S., Yang, Young S., Diaz, Damaris S., Smith, Philip L., Milhous, Wilbur K., Đoković, Dejan, Šolaja, Bogdan, "Tetraoxane antimalarials and their reaction with Fe(II)" in Journal of Medicinal Chemistry, 49, no. 13 (2006):3790-3799,
https://doi.org/10.1021/jm050966r . .

TY  - JOUR
AU  - Šolaja, Bogdan
AU  - Terzić, Nataša
AU  - Pocsfalvi, Gabriella
AU  - Gerena, L.
AU  - Tinant, Bernard
AU  - Opsenica, Dejan
AU  - Milhous, Wilbur K.
PY  - 2002
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/91
AB  - Mixed 1,2,4,5-tetraoxanes possessing simple spirocycloalkane and spirocholic acid-derived substituents were prepared and shown to have significantly higher in vitro antimalarial activity than bis-substituted tetraoxanes. Out of 41 synthesized tetraoxanes, 12 were in vitro more potent against Plasmodium falciparum chloroquine-resistant W2 clone than artemisinin, and the most potent one was 2.4 times as active as arteether. In addition, 9 compounds exhibit higher activity than chloroquine against P. falciparum chloroquine-susceptible D6 clone. Cytotoxicity was assessed for most active compounds against the Vero cell line, showing a cytotoxicity/antimalarial potency ratio of 1/(1400-9500). For the first time, tetraoxanes were screened against Mycobacterium tuberculosis with MICs as low as 4.73 μM against H37Rv strain. Mixed tetraoxanes were synthesized in a simple procedure from cholic acid methyl esters by direct coupling of steroidal gem-dihydroperoxide to simple ketones and further transformed into corresponding acids and amides.
PB  - American Chemical Society (ACS)
T2  - Journal of Medicinal Chemistry
T1  - Mixed steroidal 1,2,4,5-tetraoxanes: Antimalarial and antimycobacterial activity
VL  - 45
IS  - 16
SP  - 3331
EP  - 3336
DO  - 10.1021/jm020891g
ER  - 

@article{
author = "Šolaja, Bogdan and Terzić, Nataša and Pocsfalvi, Gabriella and Gerena, L. and Tinant, Bernard and Opsenica, Dejan and Milhous, Wilbur K.",
year = "2002",
abstract = "Mixed 1,2,4,5-tetraoxanes possessing simple spirocycloalkane and spirocholic acid-derived substituents were prepared and shown to have significantly higher in vitro antimalarial activity than bis-substituted tetraoxanes. Out of 41 synthesized tetraoxanes, 12 were in vitro more potent against Plasmodium falciparum chloroquine-resistant W2 clone than artemisinin, and the most potent one was 2.4 times as active as arteether. In addition, 9 compounds exhibit higher activity than chloroquine against P. falciparum chloroquine-susceptible D6 clone. Cytotoxicity was assessed for most active compounds against the Vero cell line, showing a cytotoxicity/antimalarial potency ratio of 1/(1400-9500). For the first time, tetraoxanes were screened against Mycobacterium tuberculosis with MICs as low as 4.73 μM against H37Rv strain. Mixed tetraoxanes were synthesized in a simple procedure from cholic acid methyl esters by direct coupling of steroidal gem-dihydroperoxide to simple ketones and further transformed into corresponding acids and amides.",
publisher = "American Chemical Society (ACS)",
journal = "Journal of Medicinal Chemistry",
title = "Mixed steroidal 1,2,4,5-tetraoxanes: Antimalarial and antimycobacterial activity",
volume = "45",
number = "16",
pages = "3331-3336",
doi = "10.1021/jm020891g"
}

Šolaja, B., Terzić, N., Pocsfalvi, G., Gerena, L., Tinant, B., Opsenica, D.,& Milhous, W. K.. (2002). Mixed steroidal 1,2,4,5-tetraoxanes: Antimalarial and antimycobacterial activity. in Journal of Medicinal Chemistry
American Chemical Society (ACS)., 45(16), 3331-3336.
https://doi.org/10.1021/jm020891g

Šolaja B, Terzić N, Pocsfalvi G, Gerena L, Tinant B, Opsenica D, Milhous WK. Mixed steroidal 1,2,4,5-tetraoxanes: Antimalarial and antimycobacterial activity. in Journal of Medicinal Chemistry. 2002;45(16):3331-3336.
doi:10.1021/jm020891g .

Šolaja, Bogdan, Terzić, Nataša, Pocsfalvi, Gabriella, Gerena, L., Tinant, Bernard, Opsenica, Dejan, Milhous, Wilbur K., "Mixed steroidal 1,2,4,5-tetraoxanes: Antimalarial and antimycobacterial activity" in Journal of Medicinal Chemistry, 45, no. 16 (2002):3331-3336,
https://doi.org/10.1021/jm020891g . .

TY  - JOUR
AU  - Opsenica, Dejan
AU  - Pocsfalvi, Gabriella
AU  - Juranić, Zorica
AU  - Tinant, Bernard
AU  - Declercq, J.-P.
AU  - Kyle, D.E.
AU  - Milhous, Wilbur K.
AU  - Šolaja, Bogdan
PY  - 2000
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/21
AB  - Cholic acid-derived 1,2,4,5-tetraoxanes were synthesized in order to explore the influence of steroid carrier on its antimalarial and antiproliferative activity in vitro. Starting with chiral ketones, cis and trans series of diastereomeric tetraoxanes were obtained, and the cis series was found to be ~2 times as active as the trans against Plasmodium falciparum D6 and W2 clones. The same tendency was observed against human melanoma (Fem-X) and human cervix carcinoma (HeLa) cell lines. The amide C(24) termini, for the first time introduced into the carrier molecule of a tetraoxane pharmacophore, significantly enhanced both antimalarial and antiproliferative activity, as compared to the corresponding methyl esters, with cis-bis(N-propylamide) being most efficient against the chloroquine-susceptible D6 clone (IC50 = 9.29 nM). cis- and trans-bis(N-propylamides) were also screened against PBMC, and PHA-stimulated PBMC, showing a cytotoxicity/antimalarial potency ratio of 1/10 000.
PB  - American Chemical Society (ACS)
T2  - Journal of Medicinal Chemistry
T1  - Cholic acid derivatives as 1,2,4,5-tetraoxane carriers: Structure and antimalarial and antiproliferative activity
VL  - 43
IS  - 17
SP  - 3274
EP  - 3282
DO  - 10.1021/jm000952f
ER  - 

@article{
author = "Opsenica, Dejan and Pocsfalvi, Gabriella and Juranić, Zorica and Tinant, Bernard and Declercq, J.-P. and Kyle, D.E. and Milhous, Wilbur K. and Šolaja, Bogdan",
year = "2000",
abstract = "Cholic acid-derived 1,2,4,5-tetraoxanes were synthesized in order to explore the influence of steroid carrier on its antimalarial and antiproliferative activity in vitro. Starting with chiral ketones, cis and trans series of diastereomeric tetraoxanes were obtained, and the cis series was found to be ~2 times as active as the trans against Plasmodium falciparum D6 and W2 clones. The same tendency was observed against human melanoma (Fem-X) and human cervix carcinoma (HeLa) cell lines. The amide C(24) termini, for the first time introduced into the carrier molecule of a tetraoxane pharmacophore, significantly enhanced both antimalarial and antiproliferative activity, as compared to the corresponding methyl esters, with cis-bis(N-propylamide) being most efficient against the chloroquine-susceptible D6 clone (IC50 = 9.29 nM). cis- and trans-bis(N-propylamides) were also screened against PBMC, and PHA-stimulated PBMC, showing a cytotoxicity/antimalarial potency ratio of 1/10 000.",
publisher = "American Chemical Society (ACS)",
journal = "Journal of Medicinal Chemistry",
title = "Cholic acid derivatives as 1,2,4,5-tetraoxane carriers: Structure and antimalarial and antiproliferative activity",
volume = "43",
number = "17",
pages = "3274-3282",
doi = "10.1021/jm000952f"
}

Opsenica, D., Pocsfalvi, G., Juranić, Z., Tinant, B., Declercq, J.-P., Kyle, D.E., Milhous, W. K.,& Šolaja, B.. (2000). Cholic acid derivatives as 1,2,4,5-tetraoxane carriers: Structure and antimalarial and antiproliferative activity. in Journal of Medicinal Chemistry
American Chemical Society (ACS)., 43(17), 3274-3282.
https://doi.org/10.1021/jm000952f

Opsenica D, Pocsfalvi G, Juranić Z, Tinant B, Declercq J, Kyle D, Milhous WK, Šolaja B. Cholic acid derivatives as 1,2,4,5-tetraoxane carriers: Structure and antimalarial and antiproliferative activity. in Journal of Medicinal Chemistry. 2000;43(17):3274-3282.
doi:10.1021/jm000952f .

Opsenica, Dejan, Pocsfalvi, Gabriella, Juranić, Zorica, Tinant, Bernard, Declercq, J.-P., Kyle, D.E., Milhous, Wilbur K., Šolaja, Bogdan, "Cholic acid derivatives as 1,2,4,5-tetraoxane carriers: Structure and antimalarial and antiproliferative activity" in Journal of Medicinal Chemistry, 43, no. 17 (2000):3274-3282,
https://doi.org/10.1021/jm000952f . .

TY  - JOUR
AU  - Bjelaković, Mira
AU  - Pavlović, Vladimir D.
AU  - Lorenc, Ljubinka
AU  - Tinant, Bernard
AU  - Declercq, Jean-Paul
PY  - 2000
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/16
AB  - The crystal structure of 14-oxo-13,14-seco-5α-cholest-13(18)-en-3β-yl acetate (2), obtained (in addition to the (E)-Δ12-isomer 3) by oxidative fragmentation of the C(13)-C(14) bond of 14α-hydroxy-5α-cholestan-3β-yl acetate (1), was determined by X-ray analysis. In addition, the configurations of the acetoxy derivatives 4-6, formed by the thermal lead tetraacetate oxidation of 1, were deduced from the relevant 1H-NMR parameters.
AB  - Kristalna struktura 14-okso-13,14-seko-5α-holest-13(18)-en-3β-il-acetata (2). koji se dobiva (pored (E)-Δ12-izomera 3) oksidativnom fragmentacijom C(13)-C(14) veze 14α-hidroksi-5α-holestan-3β-il-acetata (1) određena je analizom X-zraka. Pored toga, konfiguracije njegovih acetoksi derivata 4-6, koji se grade pri termičkoj olovo-tetraacetatnoj oksidaciji, izvedene su na osnovu odgovarajućih 1H-NMR parametara.
PB  - Serbian Chemical Society
T2  - Journal of the Serbian Chemical Society
T1  - The crystal structure of 14-oxo-13,14-seco-5α-cholest-13(18)-en-3β-yl acetate and the assignment of the configuration of its acetoxy derivatives
T1  - Kristalna struktura 14-okso-13,14-seko-5α-holest-13(18)-en-3β-il-acetata i određivanje konfiguracije njegovih acetoksi derivata
VL  - 65
IS  - 8
SP  - 541
EP  - 547
UR  - https://hdl.handle.net/21.15107/rcub_cer_16
ER  - 

@article{
author = "Bjelaković, Mira and Pavlović, Vladimir D. and Lorenc, Ljubinka and Tinant, Bernard and Declercq, Jean-Paul",
year = "2000",
abstract = "The crystal structure of 14-oxo-13,14-seco-5α-cholest-13(18)-en-3β-yl acetate (2), obtained (in addition to the (E)-Δ12-isomer 3) by oxidative fragmentation of the C(13)-C(14) bond of 14α-hydroxy-5α-cholestan-3β-yl acetate (1), was determined by X-ray analysis. In addition, the configurations of the acetoxy derivatives 4-6, formed by the thermal lead tetraacetate oxidation of 1, were deduced from the relevant 1H-NMR parameters., Kristalna struktura 14-okso-13,14-seko-5α-holest-13(18)-en-3β-il-acetata (2). koji se dobiva (pored (E)-Δ12-izomera 3) oksidativnom fragmentacijom C(13)-C(14) veze 14α-hidroksi-5α-holestan-3β-il-acetata (1) određena je analizom X-zraka. Pored toga, konfiguracije njegovih acetoksi derivata 4-6, koji se grade pri termičkoj olovo-tetraacetatnoj oksidaciji, izvedene su na osnovu odgovarajućih 1H-NMR parametara.",
publisher = "Serbian Chemical Society",
journal = "Journal of the Serbian Chemical Society",
title = "The crystal structure of 14-oxo-13,14-seco-5α-cholest-13(18)-en-3β-yl acetate and the assignment of the configuration of its acetoxy derivatives, Kristalna struktura 14-okso-13,14-seko-5α-holest-13(18)-en-3β-il-acetata i određivanje konfiguracije njegovih acetoksi derivata",
volume = "65",
number = "8",
pages = "541-547",
url = "https://hdl.handle.net/21.15107/rcub_cer_16"
}

Bjelaković, M., Pavlović, V. D., Lorenc, L., Tinant, B.,& Declercq, J.. (2000). The crystal structure of 14-oxo-13,14-seco-5α-cholest-13(18)-en-3β-yl acetate and the assignment of the configuration of its acetoxy derivatives. in Journal of the Serbian Chemical Society
Serbian Chemical Society., 65(8), 541-547.
https://hdl.handle.net/21.15107/rcub_cer_16

Bjelaković M, Pavlović VD, Lorenc L, Tinant B, Declercq J. The crystal structure of 14-oxo-13,14-seco-5α-cholest-13(18)-en-3β-yl acetate and the assignment of the configuration of its acetoxy derivatives. in Journal of the Serbian Chemical Society. 2000;65(8):541-547.
https://hdl.handle.net/21.15107/rcub_cer_16 .

Bjelaković, Mira, Pavlović, Vladimir D., Lorenc, Ljubinka, Tinant, Bernard, Declercq, Jean-Paul, "The crystal structure of 14-oxo-13,14-seco-5α-cholest-13(18)-en-3β-yl acetate and the assignment of the configuration of its acetoxy derivatives" in Journal of the Serbian Chemical Society, 65, no. 8 (2000):541-547,
https://hdl.handle.net/21.15107/rcub_cer_16 .

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 . .