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Evgenija A Djurendić, Marina P. Zaviš, M. Sakač, V. Kojić, G. Bogdanovic, K. P. Gaši
8 2008.

Synthesis and Biological Evaluation of Some A,D-Ring Modified 16,17-Secoandrostane Derivatives

Starting from 3β-hydroxy-17-oxo-16,17-secoandrost-5-ene-16-nitrile (1), the new 16,17-secoandrostane derivatives 2-11 were synthesized. Protection of the 17-oxo function of compound 1 with ethylene glycol yielded compounds 2 and 3. The Oppenauer oxidation of 2 or oxidation with H 2 O 2 in alkaline conditions gave the respective compounds 4 and 10. Epoxidation of compound 4 yielded a mixture of 4a,5a- and 4β,5β-epoxides 5 and 6 and a mixture of 4α,5α- and 4β,5β-epoxy-carboxamides 7 and 8. Opening of the oxirane ring of a mixture of compounds 5 and 6 with formic acid afforded the 4-hydroxy derivative 9. Anti-aromatase activity and in vitro cytotoxicity for three tumor cell lines (human breast adenocarcinoma ER+, MCF-7 as well as human breast adenocarcinoma ER-, MDA-MB-231, and prostate cancer, PC3) of selected compounds were evaluated. Compounds 2, 4, 9, and 10 showed a strong cytotoxicity for PC3 cells.


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