Next Article in Journal
Teaching NMR Using Online Textbooks
Previous Article in Journal
Fast Solvent-free Alkylation of Amides and Lactams under Microwave Irradiation
Article Menu

Export Article

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

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
View Full-Text   |   Download PDF [221 KB, uploaded 18 June 2014]   |  


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). View Full-Text
Keywords: Steroids; epoxyquinol; quinol; X-ray crystallography; antitumor activity Steroids; epoxyquinol; quinol; X-ray crystallography; antitumor activity

Figure 1

This is an open access article distributed under the Creative Commons Attribution License (CC BY 3.0).

Scifeed alert for new publications

Never miss any articles matching your research from any publisher
  • Get alerts for new papers matching your research
  • Find out the new papers from selected authors
  • Updated daily for 49'000+ journals and 6000+ publishers
  • Define your Scifeed now

SciFeed Share & Cite This Article

MDPI and ACS Style

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.

Show more citation formats Show less citations formats

Related Articles

Article Metrics

Article Access Statistics



[Return to top]
Molecules EISSN 1420-3049 Published by MDPI AG, Basel, Switzerland RSS E-Mail Table of Contents Alert
Back to Top