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Graphical abstract Figure. No caption available. HighlightsSynthesis of four series of pregnenolone derivatives.Comparison study between the cytotoxicity of steroids with an ester group at C‐21 or C‐3 (in four cell lines).Determination of the cytotoxic effect of the steroids with one or two &agr;,&bgr;‐unsaturated carbonyls.The steroids with 4‐fluorinated benzoic acid ester at C‐21 were cytotoxic against SKLU‐1 cell line. ABSTRACT Four series of pregnenolone derivatives having one or two &agr;,&bgr;‐unsaturated carbonyls and an ester moiety at C‐21 or C‐3 were synthetized to compare their cytotoxicity effect. The final compounds were evaluated on three human cancer cell lines: PC‐3 (prostate cancer), MCF‐7 (breast cancer), SKLU‐1 (lung cancer) and a noncancerous cell line HGF (human gingival fibroblast). Two steroids with a 4‐fluorinated benzoic acid ester at C‐21 were the most active against lung cancer cell line with IC50 of 13.1 ± 1.2 and 12.8 ± 0.5 &mgr;M and showed a low percentage of cytotoxicity for noncancerous cells (27.63 ± 2.3 and 18.39 ± 1.2% in the screening at 50 &mgr;M).