Synthesis of novel (E)-2-(4-(1H-1,2,4-triazol-1-yl)styryl)-4- (alkyl/arylmethyleneoxy)quinazoline derivatives as antimicrobial agents

Mol Divers. 2018 Feb;22(1):71-82. doi: 10.1007/s11030-017-9792-1. Epub 2017 Nov 8.

Abstract

A series of novel (E)-2-(4-(1H-1,2,4-triazol-1-yl)styryl)-4-(alkyl/arylmethyleneoxy)quinazoline derivatives (4a-4s) were synthesized in good to excellent yields, and their structures were fully characterized by [Formula: see text] NMR, [Formula: see text] NMR, HRMS and IR spectra. The structure of compound 4b was further confirmed via single-crystal X-ray diffraction analysis. The bioassay results indicated that compounds 4s, 4q and 4n inhibit phytopathogenic bacterium Xanthomonas axonopodis pv. citri (Xac) more potently than commercial bactericide bismerthiazol. However, not a single compound can effectively inhibit three pathogenic fungi tested at 50 [Formula: see text].

Keywords: 1,2,4-Triazole; Antibacterial activity; Quinazoline; Synthesis.

MeSH terms

  • Anti-Infective Agents / chemical synthesis*
  • Anti-Infective Agents / chemistry
  • Anti-Infective Agents / pharmacology*
  • Bacteria / drug effects
  • Chemistry Techniques, Synthetic*
  • Crystallography, X-Ray
  • Fungi / drug effects
  • Microbial Sensitivity Tests
  • Models, Molecular
  • Molecular Structure
  • Quinazolines / chemical synthesis*
  • Quinazolines / chemistry
  • Quinazolines / pharmacology*

Substances

  • Anti-Infective Agents
  • Quinazolines