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

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• 作者：Shweta Sharma ; Vishal Sharma ; Gurpreet Singh ; Harpreet Kaur…
• 关键词：3 ; Formylchromones ; 2 ; Chromonylimidazoles ; Antibacterial activity ; Antifungal activity ; Molecular docking
• 刊名：Journal of Chemical Biology
• 出版年：2017
• 出版时间：January 2017
• 年：2017
• 卷：10
• 期：1
• 页码：35-44
• 全文大小：
• 刊物主题：Physical Chemistry; Biological and Medical Physics, Biophysics; Cell Biology; Pharmacology/Toxicology; Biochemistry, general;
• 出版者：Springer Berlin Heidelberg
• ISSN：1864-6166
• 卷排序：10

文摘

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.