Evaluation of the lipophilicity of chalcones by RP-TLC and computational methods

Abstract

Retention behaviour of twenty-one chalcones synthesized in our laboratory was tested in three thin-layer chromatography (RP-TLC) systems (acetonitrile–water, ethanol–water and acetone–water) and chromatography parameters $$ {R}_M^0 $$ , S and C0 were calculated. The most suitable RP-TLC system (acetonitrile–water) and chromatography parameter (C0) for lipophilicity prediction of tested compounds were selected on the basis of the highest correlations with calculated logP values. In selected system, compound 12 had the highest, whereas 47 had the lowest C0 value. QSRR analysis was performed and three models representing relationships between C0 and selected molecular descriptors were created—MLR(C0), PLS(C0) and SVM(C0). Interpretation of molecular descriptors which form statistically the most reliable SVM(C0) model identified the most important structural and physico-chemical properties that influence retention behaviour of tested compounds. In addition, descriptors with the highest influence on $$ {R}_M^0 $$ as well as on C0 calculated in the remaining two RP-TLC systems were identified and interpreted.