Synthesis andin vitroanticancer activity of 23(23′)E-benzylidenespirostanols derived from steroid sapogenins


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Abstract

Graphical abstractHighlightsCondensation of spirostanes and benzaldehyde led to benzylidenspirostanes.Saponification of benzylidenspirostanes led to benzylidenspirostanols.New benzylidenspirostanols showed cytotoxicity against three cancer cell lines.The most active compound bears a trans AB core and a carbonyl group at C-12.Benzylidenespirostanols were prepared by two-step synthesis including BF3·Et2O-catalyzed aldol condensation of several acetylated steroid sapogenins with benzaldehyde followed by saponification. The obtained compounds showed moderate cytotoxicity against three cancer cell lines (T-lymphoblastic leukemia cell line CEM, breast carcinoma cell line MCF7 and cervical carcinoma cell line HeLa) and normal human fibroblasts (BJ). The most active of the five tested substances was 3c (lowest IC50 for MCF7 cells 19.9 ± 0.1 μM) without any selectivity towards human cancer and normal cells, respectively.

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