ABSTRACT A highly efficient, environmentally benign one‐pot multicomponent protocol was developed for synthesizing novel 1,3‐thiazolidin‐4‐one derivatives via microwave irradiation of 3‐pyridyl isothiocyanate, primary amines, and ethyl chloroacetate. This green methodology delivered 3‐substituted‐2‐(pyridin‐3‐ylimino)thiazolidin‐4‐ones in 2–5 min (66%–81% yields), representing a dramatic improvement over conventional reflux (3–6 h). All structures were unambiguously characterized by FT‐IR, NMR spectroscopy, and elemental analysis. Antibacterial screening against Gram‐positive ( Bacillus cereus , Staphylococcus aureus ) and Gram‐negative ( Pseudomonas aeruginosa , Escherichia coli ) pathogens revealed exceptional potency, particularly for the 3‐chlorophenyl derivative ( 8 ), which achieved 82% of ciprofloxacin's activity against E. coli (45 mm inhibition zone). Structure–activity relationships demonstrated that aromatic N‐substituents with electron‐withdrawing groups significantly enhanced antimicrobial efficacy through π‐conjugation and σ ‐hole interactions. Comprehensive computational studies (FMO analysis, ADMET profiling, and molecular docking against DNA gyrase subunit B) validated the experimental findings, revealing that compound 8 forms robust halogen‐bonded and π‐stacked complexes, acting as an allosteric inhibitor. With excellent drug‐likeness (QED = 0.777–0.913), low toxicity risks, and a favorable therapeutic window, this scaffold offers a promising platform for developing next‐generation antibacterial agents targeting resistant bacterial strains.
Ali et al. (Sat,) studied this question.
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