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Molecules 2015, 20(8), 15206-15223; doi:10.3390/molecules200815206

Synthesis and Evaluation of Selected Benzimidazole Derivatives as Potential Antimicrobial Agents

1
Chemistry Department, College of Science, King Saud University, Riyadh 11362, Saudi Arabia
2
Centre for Pharmaceutical Engineering Science, Faculty of Life Sciences, University of Bradford, Richmond Road, Bradford BD7 1DP, UK
3
Botany and Microbiology Department, College of Science, King Saud University, Riyadh 11362, Saudi Arabia
4
Department of Pharmaceutical Chemistry, College of Pharmacy, Sattam bin Abdulaziz University, Al-Kharj 11942, Saudi Arabia
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Pharmacognosy Department, College of Pharmacy, Salman bin Abdulaziz University, Al-Kharj 11942, Saudi Arabia
6
Faculty of Science and Engineering, University of Wolverhampton, Wulfruna Street, Wolverhampton WV1 1LY, UK
*
Authors to whom correspondence should be addressed.
Academic Editor: Derek J. McPhee
Received: 28 June 2015 / Revised: 9 August 2015 / Accepted: 10 August 2015 / Published: 20 August 2015
(This article belongs to the Section Medicinal Chemistry)
View Full-Text   |   Download PDF [782 KB, uploaded 20 August 2015]   |  

Abstract

A library of 53 benzimidazole derivatives, with substituents at positions 1, 2 and 5, were synthesized and screened against a series of reference strains of bacteria and fungi of medical relevance. The SAR analyses of the most promising results showed that the antimicrobial activity of the compounds depended on the substituents attached to the bicyclic heterocycle. In particular, some compounds displayed antibacterial activity against two methicillin-resistant Staphylococcus aureus (MRSA) strains with minimum inhibitory concentrations (MICs) comparable to the widely-used drug ciprofloxacin. The compounds have some common features; three possess 5-halo substituents; two are derivatives of (S)-2-ethanaminebenzimidazole; and the others are derivatives of one 2-(chloromethyl)-1H-benzo[d]imidazole and (1H-benzo[d]imidazol-2-yl)methanethiol. The results from the antifungal screening were also very interesting: 23 compounds exhibited potent fungicidal activity against the selected fungal strains. They displayed equivalent or greater potency in their MIC values than amphotericin B. The 5-halobenzimidazole derivatives could be considered promising broad-spectrum antimicrobial candidates that deserve further study for potential therapeutic applications. View Full-Text
Keywords: benzimidazole; heterocycle; antibacterial activity; antifungal activity; resistance; Gram-negative; Gram-positive benzimidazole; heterocycle; antibacterial activity; antifungal activity; resistance; Gram-negative; Gram-positive
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. (CC BY 4.0).

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MDPI and ACS Style

Alasmary, F.A.S.; Snelling, A.M.; Zain, M.E.; Alafeefy, A.M.; Awaad, A.S.; Karodia, N. Synthesis and Evaluation of Selected Benzimidazole Derivatives as Potential Antimicrobial Agents. Molecules 2015, 20, 15206-15223.

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