Chemical and Pharmaceutical Bulletin p. 1984 - 1993 (1997)
Update date:2022-09-26
Topics:
Arakawa, Kenji
Inamasu, Masanori
Matsumoto, Mamoru
Okumura, Kunihito
Yasuda, Kosuke
Akatsuka, Hidenori
Kawanami, Saburo
Watanabe, Akishige
Homma, Koichi
Saiga, Yutaka
Ozeki, Masakatsu
Iijima, Ikuo
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.
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