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Synthesis, crystallography, biological activity, and molecular modeling studies of some 3-Aryl-2-(4-(substitutedphenyl)thiazol-2-yl)acrylonitrile derivatives

Year: 2025

Type: article

Abstract: In this study, a series of 3-aryl-2-(4-(substituted phenyl)thiazol-2-yl)acrylonitrile derivatives, was synthesized and their structures were elucidated using 1H/13C-NMR, IR, HRMS and quantum crystallography methods. Ab initio quantum mechanics (QM) was applied to predict their molecular geometry and FMO parameters in aqueous medium. Molecular descriptors were calculated to predicted their druglikeness. Antimicrobial activities of the synthesized compounds were investigated against Mycobacterium tuberculosis H37Rv strain, various Gram-positive and Gram-negative bacteria, and three against Candida spp. were evaluated in vitro using isoniazid, ethambutol, ciprofloxacin, and fluconazole as reference drugs. Among the tested compounds, 2-(4-(2,4-dichlorophenyl)thiazol-2-yl)-3-(4-(trifluoromethyl)phenyl)acrylonitrile (10) was found to be the most promising antifungal agent with a minimum inhibitory concertation (MIC) value of 32 µg/ml against C. parapsilosis. Based on these findings, the title compounds serve a promising starting point for further structure-activity relationships and medicinal chemistry studies.

Source: Journal of Molecular Structure

DOI: 10.1016/j.molstruc.2025.144071