Studies on Antidiabetic Agents. II. Synthesis of 5-[4-(1-Methylcyclohexylmethoxy)-benzyl] thiazolidine-2, 4-dione (ADD-3878) and Its Derivatives

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 act...

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Published inChemical & pharmaceutical bulletin Vol. 30; no. 10; pp. 3580 - 3600
Main Authors SOHDA, TAKASHI, MIZUNO, KATSUTOSHI, IMAMIYA, EIKO, SUGIYAMA, YASUO, FUJITA, TAKESHI, KAWAMATSU, YUTAKA
Format Journal Article
LanguageEnglish
Published Japan The Pharmaceutical Society of Japan 01.10.1982
Japan Science and Technology Agency
Subjects
Animals
Hypoglycemic Agents - chemical synthesis
Male
Mice
Mice, Obese
structure-activity relationship
Thiazoles - chemical synthesis
Thiazoles - pharmacology
Thiazolidinediones
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Summary: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.
Bibliography:ObjectType-Article-1
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ISSN:0009-2363
1347-5223
DOI:10.1248/cpb.30.3580