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) β-oriented hydroxy group and β-oriented O atom bridging C(4) and C(5). The conformation of A ring in both conformers A and B is boat (B3,6 ), while rings B and C are chairs (1C4) and the five-membered D ring is in an envelope (E2) conformation. The in vitro antitumor activity of title compound and its 17β-acetoxy analogue against HeLa and Fem-x cells revealed IC50 values of 5.7 and 7.1 μM, and 2.25 and 1.58 μM, respectively. Corresponding quinols were tested on 47 cell lines with 10β-hydroxy-17β-acetoxyestra-1,4-dien-3-one being most active against leukemia SR cells (GI50 = 0.17 μM).
TY - JOUR
AU - Milić, Dragana
AU - Kapor, Agneš J.
AU - Markov, Borislava
AU - Ribar, Bela J.
AU - Strümpel, Marianna Katona
AU - Juranić, Zorica
AU - Gašić, Miroslav J.
AU - Šolaja, Bogdan
PY - 1999
UR - https://cer.ihtm.bg.ac.rs/handle/123456789/4405
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) β-oriented hydroxy group and β-oriented O atom bridging C(4) and C(5). The conformation of A ring in both conformers A and B is boat (B3,6 ), while rings B and C are chairs (1C4) and the five-membered D ring is in an envelope (E2) conformation. The in vitro antitumor activity of title compound and its 17β-acetoxy analogue against HeLa and Fem-x cells revealed IC50 values of 5.7 and 7.1 μM, and 2.25 and 1.58 μM, respectively. Corresponding quinols were tested on 47 cell lines with 10β-hydroxy-17β-acetoxyestra-1,4-dien-3-one being most active against leukemia SR cells (GI50 = 0.17 μM).
PB - MDPI
T2 - Molecules
T1 - X-ray crystal structure of 10β-hydroxy-4β,5β-epoxyestr-1-en3,17-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, Agneš J. and Markov, Borislava and Ribar, Bela J. and Strümpel, Marianna Katona and Juranić, Zorica and Gašić, Miroslav J. and Šolaja, Bogdan",
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) β-oriented hydroxy group and β-oriented O atom bridging C(4) and C(5). The conformation of A ring in both conformers A and B is boat (B3,6 ), while rings B and C are chairs (1C4) and the five-membered D ring is in an envelope (E2) conformation. The in vitro antitumor activity of title compound and its 17β-acetoxy analogue against HeLa and Fem-x cells revealed IC50 values of 5.7 and 7.1 μM, and 2.25 and 1.58 μM, respectively. Corresponding quinols were tested on 47 cell lines with 10β-hydroxy-17β-acetoxyestra-1,4-dien-3-one being most active against leukemia SR cells (GI50 = 0.17 μM).",
publisher = "MDPI",
journal = "Molecules",
title = "X-ray crystal structure of 10β-hydroxy-4β,5β-epoxyestr-1-en3,17-dione and antitumor activity of its congeners",
volume = "4",
number = "12",
pages = "338-352",
doi = "10.3390/41200338"
}
Milić, D., Kapor, A. J., Markov, B., Ribar, B. J., Strümpel, M. K., Juranić, Z., Gašić, M. J.,& Šolaja, B.. (1999). X-ray crystal structure of 10β-hydroxy-4β,5β-epoxyestr-1-en3,17-dione and antitumor activity of its congeners. in Molecules
MDPI., 4(12), 338-352.
https://doi.org/10.3390/41200338
Milić D, Kapor AJ, Markov B, Ribar BJ, Strümpel MK, Juranić Z, Gašić MJ, Šolaja B. X-ray crystal structure of 10β-hydroxy-4β,5β-epoxyestr-1-en3,17-dione and antitumor activity of its congeners. in Molecules. 1999;4(12):338-352.
doi:10.3390/41200338 .
Milić, Dragana, Kapor, Agneš J., Markov, Borislava, Ribar, Bela J., Strümpel, Marianna Katona, Juranić, Zorica, Gašić, Miroslav J., Šolaja, Bogdan, "X-ray crystal structure of 10β-hydroxy-4β,5β-epoxyestr-1-en3,17-dione and antitumor activity of its congeners" in Molecules, 4, no. 12 (1999):338-352,
https://doi.org/10.3390/41200338 . .
