Steroids 2009-11-01

Synthesis and antitumor activity of new D-seco and D-homo androstane derivatives.

Evgenija A Djurendić, Marina P Zavis, Marija N Sakac, Janos J Canadi, Vesna V Kojić, Gordana M Bogdanović, Katarina M Penov Gasi, Evgenija A. Djurendić, Marina P. Zaviš, Marija N. Sakač, Janoš J. Čanadi, Vesna V. Kojić, Gordana M. Bogdanović, Katarina M. Penov Gaši

Index: Steroids 74(12) , 983-8, (2009)

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Abstract

Starting from 3beta-hydroxy-17-oxo-16,17-secoandrost-5-ene-16-nitrile (1), the new 16,17-secoandrostane derivatives 4-9 were synthesized. On the other hand, 3beta-hydroxy-17-oxa-D-homoandrost-5-ene-16-one (10) yielded the new d-homo derivatives 12, 13 and 15. In vitro antiproliferative activity of selected compounds against three tumor cell lines (human breast adenocarcinoma ER+, MCF-7, human breast adenocarcinoma ER-, MDA-MB-231, prostate cancer AR-, PC-3, and normal fetal lung fibroblasts, MRC-5) was evaluated. Compounds 3 and 12 showed strong antiproliferative activity against PC-3 cells, the IC(50) values being 2 microM and 0.55 microM, respectively. Compounds 6 (10 microM) and 14 (9 microM) showed moderate activity against MDA-MB-231 cells. The synthesized compounds 1-3, 5-8, 10 and 12-15 were not toxic to normal fetal lung fibroblasts cells, MRC-5.