Synthesis and antibacterial activities of 1-alkyl-3-methacryloyl (acryloyl) of benzimidazolone (thione) derivatives

Int J Mol Sci. 2012;13(4):4819-4830. doi: 10.3390/ijms13044819. Epub 2012 Apr 16.

Abstract

A series of (28) 1-alkyl-3-methacryloyl (acryloyl)-benzimidazolone (thione) deriv-atives were synthesized. The structures of the new derivatives were confirmed by (1)H-NMR, (13)C-NMR and ESI-MS spectral analysis. The antibacterial activities of these compounds against several strains of bacteria, such as Bacillus cereus, Bacillus subtilis, Escherichia coli, Staphylococcus aureus and Pseudomonas aeruginosa, were evaluated by methods of paper disc-diffusion and broth mciro-dilution. Methacryloyl derivatives displayed higher antibacterial activities against tested bacterial strains than those of acryloyl derivatives in in vitro tests. A structure-activity relationship (SAR) study revealed that the presences of the methacryloyl moieties is essential to the antibacterial activities of the compounds.

Keywords: antibacterial activity; benzimidazolone (thione) derivatives; 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
  • Benzimidazoles* / chemical synthesis
  • Benzimidazoles* / chemistry
  • Benzimidazoles* / pharmacology
  • Gram-Negative Bacteria / drug effects*
  • Gram-Positive Bacteria / drug effects*
  • Microbial Sensitivity Tests
  • Structure-Activity Relationship
  • Thiones* / chemical synthesis
  • Thiones* / chemistry
  • Thiones* / pharmacology

Substances

  • Anti-Bacterial Agents
  • Benzimidazoles
  • Thiones
  • benzimidazolone