N/C-4 substituted azetidin-2-ones: synthesis and preliminary evaluation as new class of antimicrobial agents

Bioorg Med Chem Lett. 2007 Jan 15;17(2):341-5. doi: 10.1016/j.bmcl.2006.10.064. Epub 2006 Oct 26.

Abstract

A series of 3-chloro-4-(3-methoxy-4-acetyloxyphenyl)-1-[3-oxo-3-(phenylamino)propanamido] azetidin-2-ones 3a-g and 3-chloro-4-[2-hydroxy-5-(nitro substituted phenylazo)phenyl]-1-phenylazetidin-2-ones 6a-h were synthesized using appropriate synthetic route. Structures of all the synthesized compounds were established on the basis of elemental analysis and spectroscopic data. The antimicrobial activity of the synthesized compounds was screened against several microbes. Several of these molecules showed potent antimicrobial activity against Bacillus anthracis, Staphylococcus aureus and Candida albicans and significant structure-activity relationship (SAR) trends.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Anti-Bacterial Agents / chemical synthesis
  • Anti-Bacterial Agents / pharmacology
  • Anti-Infective Agents / chemical synthesis*
  • Anti-Infective Agents / pharmacology*
  • Antifungal Agents / chemical synthesis
  • Antifungal Agents / pharmacology
  • Azetidines / chemical synthesis*
  • Azetidines / pharmacology*
  • Bacteria / drug effects
  • Bacteria / growth & development
  • Cyclization
  • Drug Design
  • Drug Evaluation, Preclinical
  • Fungi / drug effects
  • Fungi / growth & development
  • Indicators and Reagents
  • Microbial Sensitivity Tests
  • Structure-Activity Relationship

Substances

  • Anti-Bacterial Agents
  • Anti-Infective Agents
  • Antifungal Agents
  • Azetidines
  • Indicators and Reagents