Facile synthesis, characterization and in vitro antibacterial efficacy of functionalized 2-substituted benzimidazole motifs


Olayinka Oyewale Ajani(1*), Olaoluwasubomi E Joseph(2), King T. Iyaye(3), Natasha October(4), Damilola V. Aderohunmu(5), Shade J. Olorunshola(6), Oluwatosin Y. Audu(7)

(1) Covenant University
(2) Covenant University
(3) Covenant University
(4) University of Pretoria
(5) Covenant University
(6) Covenant University
(7) University of Pretoria
(*) Corresponding Author


Benzimidazole is a benzo-fused imidazole that has valuable application which cut across almost every area of human existence. A series of functionalized 2-substituted benzimidazole motifs was designed and successfully synthesized via thermal cyclization of 1,2-diaminobenzene on COOH end of leucine to achieve benzimidazole derivatives 6 as the essential precursor. The coupling of the precursor 6 with benzaldehyde derivatives a-h, ketone series i-k and aryl sulfonyl chlorides l-n led to the formation of the targeted 2-substituted benzimidazole motifs 7a-n in improved yields. The targeted benzimidazole motifs were structurally authenticated through their spectral data and microanalytical parameters. The targeted final moieties were investigated for potential antimicrobial activity using agar diffusion method with gentamicin as the clinical standard. All the compounds had broad spectrum of activity with compound 7k having the highest remarkable activity with MIC of 0.98 ± 0.02 µg/mL and MBC value of 3.91 ± 0.10 µg/mL. These findings suggest that compound 7k might be a good candidate for the design of new antimicrobial small-molecule drugs.

DOI: https://doi.org/10.22146/ijc.40448

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Indonesian Journal of Chemisty (ISSN 1411-9420 / 2460-1578) - Chemistry Department, Universitas Gadjah Mada, Indonesia.

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