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

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-231,26-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.
Graphical Abstract Highlights

  • ► Three new ethylidene-oxocholestane derivatives were synthesized from spirostanic sapogenins. ► Reductive cleavage directed by 9-BBN is the pivotal reaction in their synthesis. ► Antiproliferative activity against CEM and MCF7 cancer cells was accounted. ► Cytotoxic selectivity was proved by testing compounds against tumor and normal cells. ► Cell cycle and apoptosis assays were implemented to confirm anti-cancer activity.

    Authors:   José Oscar H. Pérez-Díaz, Lucie Rárová, J. Paul Muñoz Ocampo, Nancy E. Magaña-Vergara, Norberto Farfán, Miroslav Strnad, Rosa Santillan
    Journal:   European Journal of Medicinal Chemistry
    Year:   2012
    DOI:   10.1016/j.ejmech.2012.02.020
    Publication date:   30-04-2012
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