Studies on antidiabetic agents. I. Synthesis of 5-(4-(2-methyl-2-phenylpropoxy)-benzyl)thiazolidine-2,4-dione (AL-321) and related compounds.

Abstract

A series of compounds bearing the 4-(2-methyl-2-phenylpropoxy) benzyl moiety was prepared and their hypoglycemic and hypolipidemic activities were evaluated with genetically obese and diabetic mice, yellow KK. Among these compounds, 5-[4-(2-methyl-2-phenylpropoxy) benzyl] thiazolidine-2, 4-dione (18, AL-321) was found to prossess hypoglycemic and hypolipidemic activities higher than or comparable to those of ethyl 2-chloro-3-[4-(2-methyl-2-phenylpropoxy) phenyl] propionate (1a). The acidic thiazolidine-2, 4-dione ring appeared to be essential for the activities.