Synthesis of 2-{(5-phenyl-1,3,4-Oxadiazol-2-yl)sulfanyl}-N-substituted acetamides as potential antimicrobial and hemolytic agents

Pak J Pharm Sci. 2016 May;29(3):801-9.


A new series of N-substituted derivatives of 2-{(5-phenyl-1,3,4-Oxadiazol-2-yl)sulfanyl}acetamides was synthesized. The synthesis was carried out by converting benzoic acid (1) into ethyl benzoate (2), benzohydrazide (3) and then 5-pheny-1,3,4-Oxadiazol-2-thiol (4) step by st0ep. The target compounds 6a-p were synthesized by reaction of compound 4 with equimolar ratios of different N-alkyl/aryl substituted 2-bromoacetamide (5a-p) in the presence of DMF and sodium hydride (NaH). The spectral (EI-MS, IR, (1)H-NMR) characterization of all the synthesized compounds reveal their successful synthesis. The compounds were also screened for antimicrobial & hemolytic activity and most of them were found to be active against the selected microbial species at variable extent relative to reference standards. But 6h was the most active against the selected panel of microbes. This series showed less toxicity and may be considered for further biological screening and application trial except 6m, possessing higher cytotoxicity.

Publication types

  • Comparative Study

MeSH terms

  • Acetamides / chemical synthesis*
  • Acetamides / pharmacology*
  • Acetamides / toxicity
  • Anti-Infective Agents / chemical synthesis*
  • Anti-Infective Agents / pharmacology*
  • Anti-Infective Agents / toxicity
  • Disk Diffusion Antimicrobial Tests
  • Dose-Response Relationship, Drug
  • Drug Design*
  • Hemolysis / drug effects
  • Hemolytic Agents / chemical synthesis*
  • Hemolytic Agents / pharmacology*
  • Hemolytic Agents / toxicity
  • Humans
  • Mass Spectrometry
  • Molecular Structure
  • Oxadiazoles / chemical synthesis*
  • Oxadiazoles / pharmacology*
  • Oxadiazoles / toxicity
  • Proton Magnetic Resonance Spectroscopy
  • Spectrophotometry, Infrared
  • Structure-Activity Relationship


  • Acetamides
  • Anti-Infective Agents
  • Hemolytic Agents
  • Oxadiazoles