title: Benzimidazoles as benzamide replacements within cyclohexane-based CC chemokine receptor 2 (CCR2) antagonists.
abstract: 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.
authors.affiliation: Research and Development, Bristol-Myers Squibb Company, Princeton, NJ 08543-4000, United States. robert.cherney@bms.com
authors.forename: Robert J
authors.initials: RJ
authors.lastname: Cherney
authors.forename: Ruowei
authors.initials: R
authors.lastname: Mo
authors.forename: Dayton T
authors.initials: DT
authors.lastname: Meyer
authors.forename: Anthony D
authors.initials: AD
authors.lastname: Pechulis
authors.forename: Michael A
authors.initials: MA
authors.lastname: Guaciaro
authors.forename: Yvonne C
authors.initials: YC
authors.lastname: Lo
authors.forename: Gengjie
authors.initials: G
authors.lastname: Yang
authors.forename: Persymphonie B
authors.initials: PB
authors.lastname: Miller
authors.forename: Peggy A
authors.initials: PA
authors.lastname: Scherle
authors.forename: Qihong
authors.initials: Q
authors.lastname: Zhao
authors.forename: Mary Ellen
authors.initials: ME
authors.lastname: Cvijic
authors.forename: Joel C
authors.initials: JC
authors.lastname: Barrish
authors.forename: Carl P
authors.initials: CP
authors.lastname: Decicco
authors.forename: Percy H
authors.initials: PH
authors.lastname: Carter
mesh_terms: D001562:Benzimidazoles / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D003510:Cyclohexanes / Q000737:chemistry*; D004305:Dose-Response Relationship, Drug; D015195:Drug Design; D006801:Humans; D008861:Microsomes / Q000187:drug effects; D015394:Molecular Structure; D054390:Receptors, CCR2 / Q000037:antagonists & inhibitors*; D013329:Structure-Activity Relationship
chemical_list: D001562:Benzimidazoles; C515334:CCR2 protein, human; D003510:Cyclohexanes; D054390:Receptors, CCR2; C506365:Cyclohexane