Development of a reversed-phased thin-layer chromatography method for the lipophilicity prediction of 17β-carboxamide glucocorticoid derivatives

Abstract

Octanol–water partition coefficients (log Po/w) of fifteen previously synthesized 17β-carboxamide glucocorticoid derivatives and prednisolone were determined using shake-flask method. The retention behavior of selected compounds was tested in five reversed-phased thin-layer chromatography (RP-TLC) systems, consisting of water and organic solvent (acetonitrile, acetone, ethanol 96%, methanol, or tetrahydrofuran), and chromatography parameters (RM0, S, and C0) were calculated. Simple linear regression (SLR) analysis was performed, and the correlation between log Po/w and chromatography parameters was tested. The most appropriate RP-TLC system for log Po/w prediction was that consisting of water and ethanol 96% as the mobile phase. Statisitical evaluation of the quality of models created using this system proved their reliability for log Po/w prediction of new 17β-carboxamide glucocorticoid derivatives, and the model with the most favorable statistical parameters was underlined.