A new series of isatin-Schiff base linked 1,2,3-triazole hybrids has been synthesized using CuAAC approach from (E)-3-(phenylimino)-1-(prop-2-yn-1-yl)indolin-2-one derivatives in high yield (73-91 %). These synthesized derivatives were characterized using FT-IR, 1H NMR, 13C NMR, 2D-NMR and HRMS spectral techniques. The in vitro antimicrobial activity assay proposed that most of the tested hybrids exhibited promising activity. Compound 5j displayed good significant antibacterial efficacy against P. aeruginosa and B. subtilis with MIC value of 0.0062 µmol/mL. While, 5j showed better antifungal potency against A. niger with MIC value of 0.0123 µmol/mL. The docking studies of most promising compounds were also performed with the well-known antibacterial and antifungal targets i.e. 1KZ1, 5TZ1. Molecular modelling investigations demonstrated that hybrids 5h and 5l exhibited good interactions with 1KZN and 5TZ1, with binding energies of -9.6 and -11.0 kcal/mol, respectively. Further, molecular dynamics studies of the compounds showing promising binding interactions were also carried out to study the stability of complexes of these hybrids with both the targets.
Keywords: Isatin, Schiff base, 1,2,3-Triazole hybrids, Antimicrobial activity, Docking, Molecular dynamics.
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