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Molecules 1999, 4(12), 338-352; doi:10.3390/41200338
Article

X-Ray Crystal Structure of 10β-Hydroxy-4β,5β-epoxyestr-1-en-3,17-dione and Antitumor Activity of its Congeners

1,2, 3, 3, 3, 4, 5, 1,2 and 1,*
1 Faculty of Chemistry, University of Belgrade, Studentski trg 16, PO Box 158, YU-11001 Belgrade, Yugoslavia 2 Institute of Chemistry, Technology and Metallurgy, Belgrade, Yugoslavia 3 Institute of Physics, Faculty of Sciences, University of Novi Sad, Trg Dositeja Obradovića 4, 21000, Novi Sad, Yugoslavia 4 Institut für Kristallographie, Freie Universität Berlin, Takustr.6, D-14195 Berlin, Germany 5 Institute for Oncology and Radiology of Serbia, Belgrade, Yugoslavia
* Author to whom correspondence should be addressed.
Received: 5 August 1999 / Accepted: 1 November 1999 / Published: 23 November 1999
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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 17b-acetoxy analogue against HeLa and Fem-x cells revealed IC50 values of 5.7 and 7.1 mM, and 2.25 and 1.58 mM, respectively. Corresponding quinols were tested on 47 cell lines with 10b-hydroxy-17β-acetoxyestra-1,4-dien-3-one being most active against leukemia SR cells (GI50 = 0.17 mM).
Keywords: Steroids; epoxyquinol; quinol; X-ray crystallography; antitumor activity Steroids; epoxyquinol; quinol; X-ray crystallography; antitumor activity
This is an open access article distributed under the Creative Commons Attribution License (CC BY 3.0).
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Milić, D.R.; Kapor, A.; Markov, B.; Ribar, B.; Strümpel, M.; Juranić, Z.; Gašić, M.J.; Šolaja, B.A. X-Ray Crystal Structure of 10β-Hydroxy-4β,5β-epoxyestr-1-en-3,17-dione and Antitumor Activity of its Congeners. Molecules 1999, 4, 338-352.

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