Solvent effects on the structure-activity relationship of pharmacological active 3-substituted-5,5-diphenylhydantoins

Abstract

Absorption spectra of eight 3-substituted-5,5-diphenylhydantoins have been recorded in fourteen solvents in the range 200-100 nm. The effect of solvent dipolarity/polarizability and solvent/solute hydrogen bonding interactions are analyzed by means of the linear solvation energy relationship (LSER) concept proposed by Kamlet and Taft. The lipophilic activity of the investigated hydantoins was estimated by the calculation of log(10) P values with the Advanced Chemistry Development Software. The calculated values of log(10) P were correlated with the ratio of the contributions of specific solvent interactions, and, by employing the linear dependence thus obtained, the pharmacological activity of the studied hydantoin derivatives is discussed.