TY  - JOUR
AU  - Kapor, A
AU  - Ribar, B
AU  - Strumpel, M
AU  - Gasic, MJ
AU  - Milić, Dragana
AU  - Šolaja, Bogdan A.
PY  - 2000
UR  - https://cherry.chem.bg.ac.rs/handle/123456789/387
AB  - Colourless single crystals were isolated as by-product during the synthesis of steroidal A-ring substituted 1,4-quinones (and epoxyquinols), as synthetic products with antibiotic and antitumor properties. Its structure was proposed by comparing IR, UV, H-1 and C-13 NMR spectra to the ones of quinone 2 and independently determined by an X-ray analysis, as 2 beta,3 beta-epoxyestr-5(10)-en-1,4,17-trione. Crystals belong to the monoclinic system with space group P2(1): a = 6.767(3) Angstrom, b = 7.097(5) Angstrom, 15.748(5) Angstrom, beta = 97.070(5)degrees, V = 750.6(8) Angstrom(3), Z = 2, D-x = 1.329 Mg m(-3), mu(Mo K-alpha) = 0.093 mm(-1). The structure was solved by direct methods and refined to a final R = 0.064 for 1729 reflections with I  gt  2 sigma(I). The steroidal skeleton with chiral centre at C13 possesses the S configuration defining beta-orientation of O2 atom bridging C2 and C3 atoms and beta-oriented methyl group bonded to C13 atom. The best plane through the ring A and epoxy ring plane form an angle of 89.6(2)degrees. Conformational analysis of the steroid rings are performed by calculating the ring puckering parameters and asymmetry factors. The conformation of the A ring is screw-boat S-1(6), ring B half-chair H-4(3), ring C chair C-1(4), and the five-membered D ring is half-chair H-2(1) conformation. The crystal structure is stabilised by the weak C-H ... O hydrogen bonds and van der Waals interaction. (C) 2000 Elsevier Science B.V. All rights reserved.
PB  - Elsevier Science Bv, Amsterdam
T2  - Journal of Molecular Structure
T1  - Structure and conformation of 2 beta,3 beta-epoxyestr-5(10)-en-1,4, 17-trione, spectroscopic and X-ray crystallographic studies
VL  - 522
SP  - 289
EP  - 301
DO  - 10.1016/S0022-2860(99)00363-4
ER  - 

@article{
author = "Kapor, A and Ribar, B and Strumpel, M and Gasic, MJ and Milić, Dragana and Šolaja, Bogdan A.",
year = "2000",
abstract = "Colourless single crystals were isolated as by-product during the synthesis of steroidal A-ring substituted 1,4-quinones (and epoxyquinols), as synthetic products with antibiotic and antitumor properties. Its structure was proposed by comparing IR, UV, H-1 and C-13 NMR spectra to the ones of quinone 2 and independently determined by an X-ray analysis, as 2 beta,3 beta-epoxyestr-5(10)-en-1,4,17-trione. Crystals belong to the monoclinic system with space group P2(1): a = 6.767(3) Angstrom, b = 7.097(5) Angstrom, 15.748(5) Angstrom, beta = 97.070(5)degrees, V = 750.6(8) Angstrom(3), Z = 2, D-x = 1.329 Mg m(-3), mu(Mo K-alpha) = 0.093 mm(-1). The structure was solved by direct methods and refined to a final R = 0.064 for 1729 reflections with I  gt  2 sigma(I). The steroidal skeleton with chiral centre at C13 possesses the S configuration defining beta-orientation of O2 atom bridging C2 and C3 atoms and beta-oriented methyl group bonded to C13 atom. The best plane through the ring A and epoxy ring plane form an angle of 89.6(2)degrees. Conformational analysis of the steroid rings are performed by calculating the ring puckering parameters and asymmetry factors. The conformation of the A ring is screw-boat S-1(6), ring B half-chair H-4(3), ring C chair C-1(4), and the five-membered D ring is half-chair H-2(1) conformation. The crystal structure is stabilised by the weak C-H ... O hydrogen bonds and van der Waals interaction. (C) 2000 Elsevier Science B.V. All rights reserved.",
publisher = "Elsevier Science Bv, Amsterdam",
journal = "Journal of Molecular Structure",
title = "Structure and conformation of 2 beta,3 beta-epoxyestr-5(10)-en-1,4, 17-trione, spectroscopic and X-ray crystallographic studies",
volume = "522",
pages = "289-301",
doi = "10.1016/S0022-2860(99)00363-4"
}

Kapor, A., Ribar, B., Strumpel, M., Gasic, M., Milić, D.,& Šolaja, B. A.. (2000). Structure and conformation of 2 beta,3 beta-epoxyestr-5(10)-en-1,4, 17-trione, spectroscopic and X-ray crystallographic studies. in Journal of Molecular Structure
Elsevier Science Bv, Amsterdam., 522, 289-301.
https://doi.org/10.1016/S0022-2860(99)00363-4

Kapor A, Ribar B, Strumpel M, Gasic M, Milić D, Šolaja BA. Structure and conformation of 2 beta,3 beta-epoxyestr-5(10)-en-1,4, 17-trione, spectroscopic and X-ray crystallographic studies. in Journal of Molecular Structure. 2000;522:289-301.
doi:10.1016/S0022-2860(99)00363-4 .

Kapor, A, Ribar, B, Strumpel, M, Gasic, MJ, Milić, Dragana, Šolaja, Bogdan A., "Structure and conformation of 2 beta,3 beta-epoxyestr-5(10)-en-1,4, 17-trione, spectroscopic and X-ray crystallographic studies" in Journal of Molecular Structure, 522 (2000):289-301,
https://doi.org/10.1016/S0022-2860(99)00363-4 . .

TY  - JOUR
AU  - Milić, Dragana
AU  - Kapor, A
AU  - Markov, B
AU  - Ribar, B
AU  - Strumpel, M
AU  - Juranić, Z.
AU  - Gasic, MJ
AU  - Šolaja, Bogdan A.
PY  - 1999
UR  - https://cherry.chem.bg.ac.rs/handle/123456789/426
AB  - Based on the biological properties of epoxyquinols from natural sources, the title compound was synthesised as a potential antitumor agent. Its molecular structure was partially confirmed by NMR studies. The detailed structure was established by X-ray analysis revealing two symmetry independent molecules in the asymmetric unit each consisting of four fused rings with the C(10) beta-oriented hydroxy group and beta-oriented O atom bridging C(4) and C(5). The conformation of A ring in both conformers A and B is boat (B-3,B-6), while rings B and C are chairs (C-1(4)) and the five-membered D ring is in an envelope (E-2) conformation. The in vitro antitumor activity of title compound and its 17 beta-acetoxy analogue against HeLa and Fem-x cells revealed IC50 values of 5.7 and 7.1 mu M, and 2.25 and 1.58 mu M, respectively. Corresponding quinols were tested on 47 cell lines with 10 beta-hydroxy-17 beta-acetoxyestra-1,4-dien-3-one being most active against leukemia SR cells (GI(50) = 0.17 mu M).
PB  - Mdpi Ag, Basel
T2  - Molecules
T1  - X-ray crystal structure of 10 beta-hydroxy-4 beta,5 beta P-epoxyestr-1-en-3,17-dione and antitumor activity of its congeners
VL  - 4
IS  - 12
SP  - 338
EP  - 352
DO  - 10.3390/41200338
ER  - 

@article{
author = "Milić, Dragana and Kapor, A and Markov, B and Ribar, B and Strumpel, M and Juranić, Z. and Gasic, MJ and Šolaja, Bogdan A.",
year = "1999",
abstract = "Based on the biological properties of epoxyquinols from natural sources, the title compound was synthesised as a potential antitumor agent. Its molecular structure was partially confirmed by NMR studies. The detailed structure was established by X-ray analysis revealing two symmetry independent molecules in the asymmetric unit each consisting of four fused rings with the C(10) beta-oriented hydroxy group and beta-oriented O atom bridging C(4) and C(5). The conformation of A ring in both conformers A and B is boat (B-3,B-6), while rings B and C are chairs (C-1(4)) and the five-membered D ring is in an envelope (E-2) conformation. The in vitro antitumor activity of title compound and its 17 beta-acetoxy analogue against HeLa and Fem-x cells revealed IC50 values of 5.7 and 7.1 mu M, and 2.25 and 1.58 mu M, respectively. Corresponding quinols were tested on 47 cell lines with 10 beta-hydroxy-17 beta-acetoxyestra-1,4-dien-3-one being most active against leukemia SR cells (GI(50) = 0.17 mu M).",
publisher = "Mdpi Ag, Basel",
journal = "Molecules",
title = "X-ray crystal structure of 10 beta-hydroxy-4 beta,5 beta P-epoxyestr-1-en-3,17-dione and antitumor activity of its congeners",
volume = "4",
number = "12",
pages = "338-352",
doi = "10.3390/41200338"
}

Milić, D., Kapor, A., Markov, B., Ribar, B., Strumpel, M., Juranić, Z., Gasic, M.,& Šolaja, B. A.. (1999). X-ray crystal structure of 10 beta-hydroxy-4 beta,5 beta P-epoxyestr-1-en-3,17-dione and antitumor activity of its congeners. in Molecules
Mdpi Ag, Basel., 4(12), 338-352.
https://doi.org/10.3390/41200338

Milić D, Kapor A, Markov B, Ribar B, Strumpel M, Juranić Z, Gasic M, Šolaja BA. X-ray crystal structure of 10 beta-hydroxy-4 beta,5 beta P-epoxyestr-1-en-3,17-dione and antitumor activity of its congeners. in Molecules. 1999;4(12):338-352.
doi:10.3390/41200338 .

Milić, Dragana, Kapor, A, Markov, B, Ribar, B, Strumpel, M, Juranić, Z., Gasic, MJ, Šolaja, Bogdan A., "X-ray crystal structure of 10 beta-hydroxy-4 beta,5 beta P-epoxyestr-1-en-3,17-dione and antitumor activity of its congeners" in Molecules, 4, no. 12 (1999):338-352,
https://doi.org/10.3390/41200338 . .