Chemical and Pharmaceutical Bulletin
Online ISSN : 1347-5223
Print ISSN : 0009-2363
ISSN-L : 0009-2363
Studies on Antidiabetic Agents. II. Synthesis of 5-[4-(1-Methylcyclohexylmethoxy)-benzyl] thiazolidine-2, 4-dione (ADD-3878) and Its Derivatives
TAKASHI SOHDAKATSUTOSHI MIZUNOEIKO IMAMIYAYASUO SUGIYAMATAKESHI FUJITAYUTAKA KAWAMATSU
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1982 Volume 30 Issue 10 Pages 3580-3600

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Abstract

More than 100 5-substituted thiazolidine-2, 4-diones were prepared and their hypoglycemic and hypolipidemic activities were evaluated with genetically obese and diabetic mice, yellow KK. The structure-activity relationship study showed that the 5-(4-oxybenzyl) moiety is essential for substantial activity. Among these compounds, 5-(4-cyclohexylmethoxy) benzylthiazolidine-2, 4-dione (47), 5-[4-(1-methylcyclohexylmethoxy) benzyl]-thiazolidine-2, 4-dione (49, ADD-3878) and 5-{4-[2-(3-pyridyl) ethoxy] benzyl} thiazolidine-2, 4-dione (59) exhibited the most favorable properties in terms of activity and toxicity.

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