Synthesis and effect of N-alkylation on antibacterial activity of 2-(Benzylthio) methyl-1H-benzimidazole derivatives
1 Laboratory of Constitution and Reaction of Matter, UFR Sciences of the Structures of Matter and Technology, Felix Houphouet Boigny University, Abidjan, Ivory Coast, 22 BP 582 Abidjan 22.
2 Natural Substances Unit, Laboratory of Bacteriology-Virology, Unit of Antibiotics, Natural Substances and Surveillance of Micro-organism Resistance to Anti-Infectious Diseases of the Institute Pasteur, Ivory Coast, 01 BP 490 Abidjan 01.
Research Article
GSC Biological and Pharmaceutical Sciences, 2022, 20(03), 272–279.
Article DOI: 10.30574/gscbps.2022.20.3.0370
Publication history:
Received on 17 August 2022; revised on 22 September 2022; accepted on 24 September 2022
Abstract:
In pursuit the development of novel potent and selective antibacterial agents, we synthesized twelve (12) N-alkyl 2-benzylthiomethyl-1H-benzimidazole derivatives and evaluated their antibacterial activities. Their antibacterial profile was determined with minimal inhibitory concentrations (MICs) and minimum bactericidal concentrations (MBCs) against a small set of two (2) strains Escherichia coli (Gram negative) and Staphylococcus aureus (Gram positive). These compounds are produced by the condensation reaction of 2-benzylthiomethyl-1H-benzimidazole (5) with benzyl chloride or bromide (6) in the presence of potassium carbonate (K2CO3). The panel of twelve synthetized compounds (7a-l) were characterized by NMR 1H, 13C spectroscopy, and high-resolution mass spectrometry (HRMS). The results showed that compounds 7a, 7b, 7c, 7d, 7e, 7f, 7h, 7k, and 7l were potent against Escherichia coli and Staphylococcus aureus, with significant MICs values from 140 to 290 µg/mL. On E. coli, five (5) compounds 7b, 7f, 7i, 7k and 7l showed bactericidal effects within common an N-alkylation by R3= phenyl, methyl, and CH2OH on the benzimidazole scaffold and the benzylthiol substituted by R2= Cl or CF3. This is evidence or a probe of these chemical groups implementing the bactericidal activity.
Keywords:
2-Benzythiomethyl-1H-benzimidazole; Antibacterial activity; Bactericidal effect; Bacteriostatic effect; Escherichia coli; Staphylococcus aureus
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