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 (AL-321) possessed hypoglycemic and hypolipidemic activities higher than or comparable to those of ethyl 2-chloro-3-[4-(2-methyl-2-phenylpropoxy)phenyl]propionate. The acidic thiazolidine-2,4-dione ring appeared to be essential for the activities.

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