Synthesis and aromatase inhibitory activity of some new 16E-arylidenosteroids

A new series of 16E-arylidene androstene derivatives has been synthesized and evaluated for aromatase inhibitory activity. The impact of various aryl substituents at 16 position of the steroid skeleton on aromatase inhibitory activity has been observed. The 16E-arylidenosteroids 6, 10 and 11 exhibited significant inhibition of the aromatase enzyme. 16-(4-Pyridylmethylene)-4-androstene-3,17-dione (6, IC50: 5.2 μM) and 16-(benzo-[1,3]dioxol-5-ylmethylene)androsta-1,4-diene-3,17-dione (11, IC50: 6.4 μM) were found to be approximately five times more potent in comparison to aminoglutethimide.

A new series of 16E-arylidenosteroidal derivatives possessing aromatase inhibitory activity has been synthesized and studiedFigure optionsDownload as PowerPoint slideHighlights
► A new series of 16E-arylidene steroids has been synthesized.
► Effect of 16-aryl-substitution on aromatase inhibitory activity has been studied.
► Steroids 6 and 11 were found to be five times more potent than aminoglutethimide.