Microwave-assisted synthesis of N-alkylated benzotriazole derivatives: antimicrobial studies

Bioorg Med Chem Lett. 2006 Feb 15;16(4):999-1004. doi: 10.1016/j.bmcl.2005.10.084. Epub 2005 Nov 18.

Abstract

Synthesis and characterization of N-alkylated benzotriazole derivatives 2(a-g) bearing pharmaceutically important bioactive substituents and their antimicrobial studies in vitro are described. The syntheses of the compounds were achieved by N-alkylation of the benzotriazole with different bioactive alkyl halides in presence of powdered K2CO3 in DMF solution and by microwave irradiation method with good yield compared to conventional method. The crystal structure analysis shows that compound 4'-benzotriazol-1-yl-methyl-biphenyl-2-carbonitrile 2a crystallizes in the space group P1 with cell parameters a = 8.526 (3) A, b = 12.706 (3) A, c = 7.966 (2) A, alpha = 100.89 (2) degrees , beta = 101.63 (3) degrees , gamma = 102.20(2) degrees, Volume = 801.7(4) A degrees , Z = 2 and the final R factor is 0.0559 for 6130 reflections with 218 parameters and zero restraint. This structure exhibits intermolecular hydrogen bonding. Compounds 2e, 2a showed significant antimicrobial activity.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Anti-Bacterial Agents* / chemical synthesis
  • Anti-Bacterial Agents* / pharmacology
  • Anti-Bacterial Agents* / radiation effects
  • Antifungal Agents / chemical synthesis
  • Antifungal Agents / pharmacology
  • Antifungal Agents / radiation effects
  • Bacteria / drug effects
  • Crystallization
  • Crystallography, X-Ray
  • Fungi / drug effects
  • Hydrogen Bonding
  • Microbial Sensitivity Tests
  • Microwaves*
  • Models, Molecular
  • Molecular Structure
  • Structure-Activity Relationship
  • Triazoles* / chemical synthesis
  • Triazoles* / pharmacology
  • Triazoles* / radiation effects

Substances

  • Anti-Bacterial Agents
  • Antifungal Agents
  • Triazoles
  • benzotriazole