title: Structure-activity relationships of bioisosteres of a carboxylic acid in a novel class of bacterial translation inhibitors.
abstract: The discovery and initial optimization of a novel anthranilic acid derived class of antibacterial agents which suffered from extensive protein binding has been previously reported. The structure-activity relationships around the carboxylic acid substituent are described herein. This acid was replaced by several alternative functional groups in attempts to retain bioactivity while reducing protein binding. Only groups with an acidic proton retained activity, and analogs containing those groups maintained the protein binding inherent to this class of antibacterial agents.
authors.affiliation: Medicinal Chemistry, Pharmacia Corporation, 301 Henrietta Street, Kalamazoo, MI 49001, USA.
authors.forename: J Craig
authors.initials: JC
authors.lastname: Ruble
authors.forename: Brian D
authors.initials: BD
authors.lastname: Wakefield
authors.forename: Gregg M
authors.initials: GM
authors.lastname: Kamilar
authors.forename: Keith R
authors.initials: KR
authors.lastname: Marotti
authors.forename: Earline
authors.initials: E
authors.lastname: Melchior
authors.forename: Michael T
authors.initials: MT
authors.lastname: Sweeney
authors.forename: Gary E
authors.initials: GE
authors.lastname: Zurenko
authors.forename: Donna L
authors.initials: DL
authors.lastname: Romero
mesh_terms: D001419:Bacteria / Q000187:drug effects* / Q000235:genetics; D002264:Carboxylic Acids / Q000737:chemistry* / Q000494:pharmacology*; D008826:Microbial Sensitivity Tests; D014176:Protein Biosynthesis / Q000187:drug effects*; D013329:Structure-Activity Relationship
chemical_list: D002264:Carboxylic Acids