Molecular design of anti-MRSA agents based on the anacardic acid scaffold

Bioorg Med Chem. 2007 Sep 15;15(18):6236-41. doi: 10.1016/j.bmc.2007.06.022. Epub 2007 Jun 14.

Abstract

A series of anacardic acid analogues possessing different side chains viz. phenolic, branched, and alicyclic were synthesized and their antibacterial activity tested against methicillin-resistant Staphylococcus aureus (MRSA). The maximum activity against this bacterium occurred with the branched side-chain analogue, 6-(4',8'-dimethylnonyl)salicylic acid, and the alicyclic side-chain analogue, 6-cyclododecylmethyl salicylic acid, with the minimum inhibitory concentration (MIC) of 0.39 microg/mL, respectively. This activity was superior to that of the most potent antibacterial anacardic acid isolated from the cashew Anacardium occidentale (Anacardiaceae), apple and nut, that is, the 6-[8'(Z),11'(Z),14'-pentadecatrienyl]salicylic acid.

MeSH terms

  • Anacardic Acids / chemical synthesis
  • Anacardic Acids / chemistry
  • Anacardic Acids / pharmacology*
  • Anacardium / chemistry
  • Anti-Bacterial Agents / chemical synthesis
  • Anti-Bacterial Agents / chemistry
  • Anti-Bacterial Agents / pharmacology*
  • Drug Design
  • Malus / chemistry
  • Methicillin / pharmacology
  • Methicillin Resistance*
  • Microbial Sensitivity Tests
  • Nuts / chemistry
  • Staphylococcus aureus / drug effects*
  • Structure-Activity Relationship

Substances

  • 6-(4',8',14'-pentadecatrienyl)salicylic acid
  • 6-(4',8'-dimethylnonyl)salicylic acid
  • Anacardic Acids
  • Anti-Bacterial Agents
  • anacardic acid
  • Methicillin