Synthesis and biological activity of 23-ethylidene-26-hydroxy-22-oxocholestane derivatives from spirostanic sapogenins

  • Eur J Med Chem. 2012 May:51:67-78. doi: 10.1016/j.ejmech.2012.02.020.
José Oscar H Pérez-Díaz  1 ,  Lucie Rárová ,  J Paul Muñoz Ocampo ,  Nancy E Magaña-Vergara ,  Norberto Farfán ,  Miroslav Strnad ,  Rosa Santillan
Affiliations
  • 1. Departamento de Química, Centro de Investigación y de Estudios Avanzados del IPN, Apdo. Postal 14-740, 07000 México DF, Mexico.
PMID: 22417637 DOI: 10.1016/j.ejmech.2012.02.020
Abstract

The synthesis and biological evaluation of three new cholestane frameworks of the type: (25R)-3β,16β-Diacetoxy-23-ethylidene-26-hydroxy-22-oxocholestane, starting from spirostanic sapogenins of the 25R series, is described. The compounds were obtained by the reductive cleavage of the F ring of 22-oxo-23(1),26-epoxycholestane derivatives using 9-BBN. These modified derivatives exhibit cytotoxic activity against CEM and MCF7 cells and are able to induce Apoptosis in them. Its effect on the cell cycle was determined.