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2-(chromon-3-yl)imidazole derivatives as potential antimicrobial agents: synthesis, biological evaluation and molecular docking studies

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Journal of Chemical Biology

Abstract

A series of novel 2-(chromon-3-yl)-4,5-diphenyl-1H-imidazoles (4a-h) were synthesized by one pot condensation of substituted 3-formylchromones (1a-h), benzil (2) and ammonium acetate (3) in refluxing acetic acid at 110 °C under N2 atmosphere. Allylation of compounds 4a-h with allyl bromide in the presence of fused K2CO3 furnished N-allyl-2-(chromon-3-yl)-4,5-diphenyl-1H-imidazoles (6a-h). The synthesized compounds were characterized spectroscopically and evaluated for in vitro antimicrobial activity against various pathogenic bacterial and fungal strains by disc diffusion method. Compounds bearing electron withdrawing substituents such as bromo (4f) showed significant inhibitory activity against S. cerevisiae (MIC 1.4 μg/ml) and 4g containing chloro substituent, displayed more inhibitory potential against C. albicans (MIC 1.5), as compared to the standard drugs. Compounds 6a and 4c exhibit remarkable inhibitory potential against B. subtilis with MIC 0.98 and 1.23, respectively. The time kill assay for active compound 6a was performed by viable cell count (VCC) method to elucidate the microbicidal nature of 2-(chromon-3-yl)imidazoles. A molecular docking study of most active compounds with target ‘lanosterol 14α-demethylase’ (CYP51) was performed to unravel the mode of antifungal action.

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Acknowledgements

We sincerely express our thanks to the University Grant Commission (UGC) for providing support and funds to our university to generate necessary research facilities.

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Authors and Affiliations

  1. Bio-organic and Photochemistry Laboratory, Department of Pharmaceutical Sciences, Guru Nanak Dev University, Amritsar, Punjab, -143005, India

    Shweta Sharma, Vishal Sharma, Gurpreet Singh & Mohan Paul S. Ishar

  2. Department of Microbiology, Guru Nanak Dev University, Amritsar, Punjab, -143005, India

    Harpreet Kaur

  3. Department of Pharmacy, School of Chemical Sciences and Pharmacy, Central University of Rajasthan, Ajmer, Rajasthan, 305817, India

    Shubham Srivastava

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  1. Shweta Sharma
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  2. Vishal Sharma
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Correspondence to Mohan Paul S. Ishar.

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Sharma, S., Sharma, V., Singh, G. et al. 2-(chromon-3-yl)imidazole derivatives as potential antimicrobial agents: synthesis, biological evaluation and molecular docking studies. J Chem Biol 10, 35–44 (2017). https://doi.org/10.1007/s12154-016-0162-8

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