Synthesis and Antimicrobial Activity of Nitrobenzyl-oxy-phenol Derivatives

Biol Pharm Bull. 2016;39(11):1888-1892. doi: 10.1248/bpb.b16-00608.

Abstract

Two hydroquinone derivatives were prepared and their antimicrobial activity evaluated. Their minimum inhibitory concentrations (MICs) were determined using a broth dilution method. Gentamycin and ciprofloxacin were used as reference antibiotics. The antimicrobial activity of 4-(benzyloxy)phenol (monobenzone) was also evaluated based on its structural similarity to the new compounds; activity was comparable to that of 3,5-dimethyl-4-((4-nitrobenzyl)oxy)phenol (4a). 2,3,5-Trimethyl-4-((4-nitrobenzyl)oxy)phenol (4b) exhibited the best antibacterial activity against both clinical isolates and type strain of Moraxella catarrhalis (M. catarrhalis), with a MIC value of 11 µM, comparable to ciprofloxacin 9 µM.

MeSH terms

  • Anti-Bacterial Agents / chemical synthesis
  • Anti-Bacterial Agents / chemistry
  • Anti-Bacterial Agents / pharmacology*
  • Bacteria / drug effects*
  • Bacteria / growth & development
  • Microbial Sensitivity Tests
  • Phenols / chemical synthesis
  • Phenols / chemistry
  • Phenols / pharmacology*

Substances

  • Anti-Bacterial Agents
  • Phenols