Exploration of (3-benzyl-5-hydroxyphenyl)carbamates as new antibacterial agents against Gram-positive bacteria

Arch Pharm (Weinheim). 2020 Mar;353(3):e1900294. doi: 10.1002/ardp.201900294. Epub 2020 Jan 2.

Abstract

A series of (3-benzyl-5-hydroxyphenyl)carbamates were evaluated as new antibacterial agents. Several compounds showed potent inhibitory activity against sensitive and drug-resistant Gram-positive bacteria. The compounds are ineffective against all tested Gram-negative bacteria. The structure of the ester group exerted a profound effect on antibacterial activity. 4,4-Dimethylcyclohexanyl carbamate 6h exhibited the most potent inhibitory activity against the standard and clinically isolated Staphylococcus aureus, Staphylococcus epidermidis, and Enterococcus faecalis (minimum inhibitory concentration = 4-8 µg/ml) strains. The preliminary experimental evidence indicated that these carbamates target the bacterial cell wall and share a similar mechanism of action with vancomycin.

Keywords: MRSA; antibacterial activity; carbamate.

MeSH terms

  • Anti-Bacterial Agents / chemical synthesis
  • Anti-Bacterial Agents / chemistry
  • Anti-Bacterial Agents / pharmacology*
  • Carbamates / chemical synthesis
  • Carbamates / chemistry
  • Carbamates / pharmacology*
  • Drug Screening Assays, Antitumor
  • Enterococcus faecalis / drug effects*
  • Microbial Sensitivity Tests
  • Molecular Structure
  • Staphylococcus aureus / drug effects*
  • Staphylococcus epidermidis / drug effects*
  • Structure-Activity Relationship

Substances

  • Anti-Bacterial Agents
  • Carbamates