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 abstractFigure optionsDownload full-size imageDownload as PowerPoint slideHighlights► 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.