Synthesis, structure and solvatochromism of 5-methyl-5-(3-or 4-substituted phenyl)hydantoins

Abstract

Several 5-methyl-5-(3- or 4-substituted phenyl)hydantoins were prepared and their ultraviolet absorption spectra were recorded in the region 200-400 nm in twelve solvents of different polarity. The effect of solvent dipolarity/ polarizability and solvent/solute hydrogen bonding interactions were 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 calculation of log P values with Advanced Chemistry Development Software. The calculated values of log P were correlated with the contribution of hydrogen bond donor-solvent interactions. By employing the thus obtained linear dependence, the pharmacological activity of the studied hydantoin derivatives is discussed.

U okviru proučavanja uticaja strukture na farmakološku aktivnost hidantoina, u ovom radu sintetizovano je četrnaest jedinjenja i određeni su njihovi UV apsorpcioni maksimumi u dvanaest rastvarača različite polarnosti. Apsorpcioni maksimumi su korelisani Kamlet-Taftovom (Kamlet-Taft) solvatohromnom jednačinom i izvršena je kvantitativna procena proton-donorskih i proton-akceptorskih karakteristika proučavanih jedinjenja, koje su od velikog značaja za njihovu fiziološku aktivnost. Izračunate vrednosti log P korelisane su sa udelom proton-donorskih karakteristika rastvarača i na osnovu dobijenih linearnih zavisnosti za molekule sa umerenim elktron-donorskim i elektron-akceptorskim supstituentima, diskutovana je veza između farmakološke aktivnosti hidantoina i interakcija sa molekulima rastvarača.