Bioisosteric replacements of the pyrazole moiety of rimonabant: synthesis, biological properties, and molecular modeling investigations of thiazoles, triazoles, and …

…, HH van Stuivenberg, HKAC Coolen…

Index: Lange, Jos H. M.; Van Stuivenberg, Herman H.; Coolen, Hein K. A. C.; Adolfs, Tiny J. P.; McCreary, Andrew C.; Keizer, Hiskias G.; Wals, Henri C.; Veerman, Willem; Borst, Alice J. M.; De Looff, Wouter; Verveer, Peter C.; Kruse, Chris G. Journal of Medicinal Chemistry, 2005 , vol. 48, # 6 p. 1823 - 1838

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Citation Number: 136

Abstract

Series of thiazoles, triazoles, and imidazoles were designed as bioisosteres, based on the 1, 5-diarylpyrazole motif that is present in the potent CB1 receptor antagonist rimonabant (SR141716A, 1). A number of target compounds was synthesized and evaluated in cannabinoid (hCB1 and hCB2) receptor assays. The thiazoles, triazoles, and imidazoles elicited in vitro CB1 antagonistic activities and in general exhibited considerable CB1 vs ...