Preparation, crystal structure and prodrug studies of genistein benzensulfonate

Abstract

4'-ethyl-7-phenylsulfonylgenistein (EPG, 3), a potential prodrug for genistein (1), was synthesized in high yield and its crystal structure was reported firstly. It possesses better physical and chemical properties such as solubility, lipid/water partition coefficient, LogP, and hydrolysis kinetics than its original form. The LogP value (2.07) and the half-life of the hydrolysis value (13.4 h) show that its oral bioavailability is possibly improved evidently compared with that of genistein. These results indicate that EPG can be considered a potential prodrug for genistein.