Structure-activity relationships of bioisosteres of a carboxylic acid in a novel class of bacterial translation inhibitors

Bioorg Med Chem Lett. 2007 Jul 15;17(14):4040-3. doi: 10.1016/j.bmcl.2007.04.074. Epub 2007 Apr 27.

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.

MeSH terms

  • Bacteria / drug effects*
  • Bacteria / genetics
  • Carboxylic Acids / chemistry*
  • Carboxylic Acids / pharmacology*
  • Microbial Sensitivity Tests
  • Protein Biosynthesis / drug effects*
  • Structure-Activity Relationship

Substances

  • Carboxylic Acids