Synthesis and antimicrobial activity of polyhalobenzonitrile quinazolin-4(3H)-one derivatives

Bioorg Med Chem Lett. 2013 Nov 1;23(21):5958-63. doi: 10.1016/j.bmcl.2013.08.068. Epub 2013 Aug 23.

Abstract

A novel series of polyhalobenzonitrile quinazolin-4(3H)-one derivatives were synthesized and characterized by NMR, IR, MS, and HRMS spectra. All of the newly prepared compounds were screened for antimicrobial activities against four strains of bacteria (Gram-positive bacterial: Staphylococcus aureus and Bacillus cereus; Gram-negative bacterial: Escherichia coli and Pseudomonas aeruginosa) and one strain of fungi (Candida albicans). Among the synthesized compounds, 5-(dimethylamino)-8-(2,4,5-trichloro-isophthalonitrile) quinazolin-4(3H)-one (7k) exhibited significant activity towards Gram-positive bacterial, Gram-negative bacterial, and the fungi strains. The MIC (0.8-3.3μg/mL) and MBC (2.6-7.8μg/mL) for this compound were close to those of nofloxacin, chlorothalonil, and fluconazole, making it the most potent antimicrobial agents in the series.

Keywords: Antimicrobial activity; Fungi strains; Gram-negative bacterial; Gram-positive bacterial; Polyhalobenzonitrile quinazolin-4(3H)-one; Synthesis.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Anti-Bacterial Agents / chemical synthesis
  • Anti-Bacterial Agents / chemistry
  • Anti-Bacterial Agents / pharmacology
  • Anti-Infective Agents / chemical synthesis
  • Anti-Infective Agents / chemistry*
  • Anti-Infective Agents / pharmacology*
  • Antifungal Agents / chemical synthesis
  • Antifungal Agents / chemistry
  • Antifungal Agents / pharmacology
  • Bacteria / drug effects*
  • Bacterial Infections / drug therapy
  • Candida albicans / drug effects*
  • Candidiasis / drug therapy
  • Humans
  • Microbial Sensitivity Tests
  • Quinazolines / chemical synthesis
  • Quinazolines / chemistry*
  • Quinazolines / pharmacology*

Substances

  • Anti-Bacterial Agents
  • Anti-Infective Agents
  • Antifungal Agents
  • Quinazolines