Novel Benzoxazole 2,4-Thiazolidinediones as Potent Hypoglycemic Agents. Synthesis and Structure-Activity Relationships.

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  • Novel Benzoxazole 2 4 Thiazolidinedione

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A new series of benzoxazole 2, 4-thiazolidinediones was synthesized and evaluated for hypoglycemic activity in genetically obese and diabetic yellow KK mice. 2-Arymethyl- and 2-(heteroarhylmethyl)benzoxazole derivatives showed far more potent activity than known 2, 4-thiazolidinedione derivatives such as ciglitazone, troglitazone and pioglitazone. A facile synthesis of benzoxazole 2, 4-thiazolidinediones was also established using aminophenol 2, 4-thiazolidinedione (11) as a key intermediate. Details of synthesis and structure-activity relationships for this series are described.

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