Benzimidazoles as benzamide replacements within cyclohexane-based CC chemokine receptor 2 (CCR2) antagonists

We describe the design, synthesis, and evaluation of benzimidazoles as benzamide replacements within a series of trisubstituted cyclohexane CCR2 antagonists. We describe the design, synthesis, and evaluation of benzimidazoles as benzamide replacements within a series of trisubstituted cyclohexane CC...

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Published in:Bioorganic & medicinal chemistry letters 2012-10, Vol.22 (19), p.6181-6184
Main Authors: Cherney, Robert J., Mo, Ruowei, Meyer, Dayton T., Pechulis, Anthony D., Guaciaro, Michael A., Lo, Yvonne C., Yang, Gengjie, Miller, Persymphonie B., Scherle, Peggy A., Zhao, Qihong, Cvijic, Mary Ellen, Barrish, Joel C., Decicco, Carl P., Carter, Percy H.
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Language:eng
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Summary:We describe the design, synthesis, and evaluation of benzimidazoles as benzamide replacements within a series of trisubstituted cyclohexane CCR2 antagonists. We describe the design, synthesis, and evaluation of benzimidazoles as benzamide replacements within a series of trisubstituted cyclohexane CCR2 antagonists. 7-Trifluoromethylbenzimidazoles displayed potent binding and functional antagonism of CCR2 while being selective over CCR3. These benzimidazoles were also incorporated into lactam-containing antagonists, thus completely eliminating the customary bis-amide.
ISSN:0960-894X
1464-3405