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).
CITATION STYLE
Milić, D. R., Kapor, A., Markov, B., Ribar, B., Strümpel, M., Juranić, Z., … Šolaja, B. A. (1999). X-ray crystal structure of 10β-hydroxy-4β,5β-epoxyestr-1-en3,17-dione and antitumor activity of its congeners. Molecules, 4(12), 338–352. https://doi.org/10.3390/41200338
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