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.

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► 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.