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
1999
Autori
Milić, DraganaKapor, A
Markov, B
Ribar, B
Strumpel, M
Juranić, Z.
Gasic, MJ
Šolaja, Bogdan A.
Članak u časopisu (Objavljena verzija)
Metapodaci
Prikaz svih podataka o dokumentuApstrakt
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...).
Ključne reči:
steroids / epoxyquinol / quinol / X-ray crystallography / antitumor activityIzvor:
Molecules, 1999, 4, 12, 338-352Izdavač:
- Mdpi Ag, Basel
DOI: 10.3390/41200338
ISSN: 1420-3049
WoS: 000084728400001
Scopus: 2-s2.0-0000703525
Kolekcije
Institucija/grupa
Hemijski fakultet / Faculty of ChemistryTY - 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 . .