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Studies on antidiabetic agents. II. Synthesis of 5-(4-(1-methylcyclohexylmethoxy)-benzyl)thiazolidine-2,4-dione (ADD-3878) and its derivatives.
Chemical and Pharmaceutical Bulletin · 1982 · Vol. 30(10) · pp. 3580–3600
Takashi Sohda✉(Takeda (Japan))Katsutoshi Mizuno(Takeda (Japan))Eiko Imamiya(Takeda (Japan))Yasuo Sugiyama(Takeda (Japan))Takeshi Fujita(Takeda (Japan))Y. Kawamatsu(Takeda (Japan))
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.
Eicosanoids and Hypertension PharmacologySynthesis and biological activityInflammatory mediators and NSAID effectsChemistryThiazolidineMoietyBiological activityStereochemistryPharmacologyBiochemistryIn vitro
MeSH terms
AnimalsHypoglycemic AgentsMaleMice, ObeseThiazolesThiazolidinedionesMice
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