Design, Synthesis and Antibacterial Evaluation of Compounds Based on New Benzoxepine-oxime-1,2,3-triazole Hybrid

Mini Rev Med Chem. 2018;18(9):803-809. doi: 10.2174/1389557517666170717123741.

Abstract

Background: A library of compounds related to the new benzoxepine-oxime-1,2,3-triazole hybrid was created as probable antibacterial agents. Their synthesis involved a Cu-catalyzed azidealkyne cycloaddition (CuAAC) as a key step to construct the desired 1,2,3-triazole ring. Thus the click reaction between the appropriate alkyne containing the benzoxepine-oxime framework with aryl azides afforded the target compounds in good yields.

Method: To assess their antibacterial properties all the synthesized compounds were tested using four bacterial strains consisting of one Gram-positive and three Gram-negative species.

Results & conclusion: These compounds were generally found to be effective towards gram -ve species and one of them showed selective cytotoxicity against lung cancer cell line.

Keywords: 1,2,3-triazole; Antibacterial; benzoxepine; erythromycin; hybrid; oxime..

MeSH terms

  • Anti-Bacterial Agents / chemical synthesis
  • Anti-Bacterial Agents / chemistry
  • Anti-Bacterial Agents / pharmacology*
  • Antineoplastic Agents / chemical synthesis
  • Antineoplastic Agents / chemistry
  • Antineoplastic Agents / pharmacology*
  • Benzoxepins / chemical synthesis
  • Benzoxepins / chemistry
  • Benzoxepins / pharmacology*
  • Cell Line, Tumor
  • Cell Proliferation / drug effects
  • Dose-Response Relationship, Drug
  • Drug Design*
  • Drug Screening Assays, Antitumor
  • Escherichia coli / drug effects
  • Humans
  • Klebsiella pneumoniae / drug effects
  • Microbial Sensitivity Tests
  • Molecular Structure
  • Oximes / chemical synthesis
  • Oximes / chemistry
  • Oximes / pharmacology*
  • Pseudomonas aeruginosa / drug effects
  • Staphylococcus aureus / drug effects
  • Structure-Activity Relationship
  • Triazoles / chemical synthesis
  • Triazoles / chemistry
  • Triazoles / pharmacology*

Substances

  • Anti-Bacterial Agents
  • Antineoplastic Agents
  • Benzoxepins
  • Oximes
  • Triazoles