title: 2-(chromon-3-yl)imidazole derivatives as potential antimicrobial agents: synthesis, biological evaluation and molecular docking studies.
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 compounds4a-hwith allyl bromide in the presence of fused K2CO3furnishedN-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 asbromo(4f) showed significant inhibitory activity againstS.cerevisiae(MIC 1.4 μg/ml) and4gcontainingchlorosubstituent, displayed more inhibitory potential againstC.albicans(MIC 1.5), as compared to the standard drugs. Compounds6aand4cexhibit remarkable inhibitory potential againstB.subtiliswith MIC 0.98 and 1.23, respectively. The time kill assay for active compound6awas 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.
authors.affiliation: Bio-organic and Photochemistry Laboratory, Department of Pharmaceutical Sciences, Guru Nanak Dev University, Amritsar, Punjab -143005 India.
authors.forename: Shweta
authors.initials: S
authors.lastname: Sharma
authors.affiliation: Bio-organic and Photochemistry Laboratory, Department of Pharmaceutical Sciences, Guru Nanak Dev University, Amritsar, Punjab -143005 India.
authors.forename: Vishal
authors.initials: V
authors.lastname: Sharma
authors.affiliation: Bio-organic and Photochemistry Laboratory, Department of Pharmaceutical Sciences, Guru Nanak Dev University, Amritsar, Punjab -143005 India.
authors.forename: Gurpreet
authors.initials: G
authors.lastname: Singh
authors.affiliation: Department of Microbiology, Guru Nanak Dev University, Amritsar, Punjab -143005 India.
authors.forename: Harpreet
authors.initials: H
authors.lastname: Kaur
authors.affiliation: Department of Pharmacy, School of Chemical Sciences and Pharmacy, Central University of Rajasthan, Ajmer, Rajasthan 305817 India.
authors.forename: Shubham
authors.initials: S
authors.lastname: Srivastava
authors.affiliation: Bio-organic and Photochemistry Laboratory, Department of Pharmaceutical Sciences, Guru Nanak Dev University, Amritsar, Punjab -143005 India.
authors.forename: Mohan Paul S
authors.initials: MP
authors.lastname: Ishar
keywords: 2-Chromonylimidazoles; 3-Formylchromones; Antibacterial activity; Antifungal activity; Molecular docking