Arakawa K, Inamasu M, Matsumoto M, Okumura K, Yasuda K, Akatsuka H, Kawanami S, Watanabe A, Homma K, Saiga Y, Ozeki M, Iijima I
Lead Optimization Research Laboratory, Tanabe Seiyaku Co., Ltd., Saitama, Japan.
Chem Pharm Bull (Tokyo). 1997 Dec;45(12):1984-93. doi: 10.1248/cpb.45.1984.
A new series of benzoxazole 2,4-thiazolidinediones was synthesized and evaluated for hypoglycemic activity in genetically obese and diabetic yellow KK mice. 2-Arylmethyl- and 2-(heteroarylmethyl)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.
