Thiazole as a carbonyl bioisostere. A novel class of highly potent and selective 5-HT3 receptor antagonists

T Rosen, AA Nagel, JP Rizzi, JL Ives…

Index: Rosen, Terry; Nagel, Arthur A.; Rizzi, James P.; Ives, Jeffrey L.; Daffeh, June B.; et al. Journal of Medicinal Chemistry, 1990 , vol. 33, # 10 p. 2715 - 2720

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Citation Number: 43

Abstract

A novel structural class of highly potent and selective 5-HT3 receptor antagonists is described. The compounds in this new series contain a thiazole moiety linking an aromatic group and a nitrogen-containing basic region; the thiazole group appears to be acting as a carbonyl bioisostere in this system. An optimized member of this series, 4-(2- methoxyphenyl)-2-[[4 (5)-methyl-5 (4)-imidazolyl] methyl] thiazole (5), exhibits oral activity ...