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X-Ray Crystal Structure of 10β-Hydroxy-4β,5β-epoxyestr-1-en-3,17-dione and Antitumor Activity of its Congeners
Faculty of Chemistry, University of Belgrade, Studentski trg 16, PO Box 158, YU-11001 Belgrade, Yugoslavia
Institute of Chemistry, Technology and Metallurgy, Belgrade, Yugoslavia
Institute of Physics, Faculty of Sciences, University of Novi Sad, Trg Dositeja Obradovića 4, 21000, Novi Sad, Yugoslavia
Institut für Kristallographie, Freie Universität Berlin, Takustr.6, D-14195 Berlin, Germany
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
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
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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.
Milić DR, Kapor A, Markov B, Ribar B, Strümpel M, Juranić Z, Gašić MJ, Šolaja BA. X-Ray Crystal Structure of 10β-Hydroxy-4β,5β-epoxyestr-1-en-3,17-dione and Antitumor Activity of its Congeners. Molecules. 1999; 4(12):338-352.
Milić, Dragana R.; Kapor, Agneš; Markov, Borislava; Ribar, Bela; Strümpel, Marianne; Juranić, Zorica; Gašić, Miroslav J.; Šolaja, Bogdan A. 1999. "X-Ray Crystal Structure of 10β-Hydroxy-4β,5β-epoxyestr-1-en-3,17-dione and Antitumor Activity of its Congeners." Molecules 4, no. 12: 338-352.