The lipophilicity estimation of 5-arylidene derivates of (2-thio)hydantoin with antimycobacterial activity

Abstract

The lipophilicity of antituberculotic 5-arylidene derivatives of (thio)hydantoin, thioacetazone and isoniazid has been determined by reversed-phase thin-layer chromatography (RP-TLC). Mixtures of acetone and water (with acetone content 60-85%) were used as the mobile phase. The RM (relative lipophilicity) of each compound (except isoniazid) decreased linearly with the increasing concentration of acetone. The partition coefficients (log P) of the compounds were calculated by the use of eight computer programs (ClogP, KowWin, XlogP, AlogPs, CAChe, Pallas, Interactive analysis and Slipper) and compared with the experimental lipophilicity (RM0). According to the observations the best tools for in silico predicting log P of (2-thio)hydantoins are programs KowWin and AlogPs. Copyright © 2007 John Wiley & Sons, Ltd.