TB Research

Microwave-assisted synthesis and in vitro antimycobacterial evaluation of some new N-benzylidene-1H-benzo[d]imidazol-6-amine derivatives

Mazen Almehmadi, Abdualziz Alsharif, Mamdouh Allahyani, Mohammad Asif

Indian Journal of Heterocyclic Chemistry · 2024-09

Abstract

N-Benzylidene-1H-benzo[d]-imidazol-6-amines (2a-f) were synthesized by the reaction between 1H-benzo[d] imidazol-6-amine and substituted aromatic aldehydes in the presence of ethyl alcohol and glacial acetic acid using microwave irradiation technique. The structures of the compounds were determined using elemental analysis, infrared, 1HNMR, and MS spectrum data. The microplate alamar blue assay method was used to test the synthesized compounds for their in vitro antimycobacterial activity against strains of Mycobacterium tuberculosis H37RV strain. Among tested compounds, compound 2a with a minimal inhibitory concentration (MIC) value of 6.25 μg/mL and compound 2b with a MIC value of 3.125 μg/mL showed better antitubercular activity than pyrazinamide and streptomycin with a MIC value of 3.125 μg/mL and 6.25 μg/mL, respectively. The electron-withdrawing group (-Cl and -NO2) substituted derivatives exhibited better activity than the electron-donating group (-OH, -CH3, and -OCH3) substituted derivatives.. KEYWORDS :Benzimidazole, Schiff base, Microwave method, Antitubercular activity.

MeSH terms

  • Antimycobacterial
  • Amine gas treating
  • In vitro
  • Chemistry
  • Combinatorial chemistry
  • Stereochemistry