Molecular docking and computational assessment of spectroscopic analysis of ethyl 3-(4-chloro-2-methylphenylamino)-3-phenylacrylate as a potential antibacterial agent

Abstract

A novel enamino ester, ethyl 3-(4-chloro-2-methylphenylamino)-3-phenylacrylate 3, was synthesized and structurally characterized. Density functional theory (DFT) calculations at the B3LYP-D3/6-311++G(d,p) level were used to investigate its molecular geometry and predict NMR chemical shifts, which showed good agreement with experimental data. Electronic properties, including the HOMO–LUMO gap, Fukui functions, and molecular electrostatic potential (MEP) surface, indicated both chemical stability and potential reactive sites. Molecular docking analysis revealed promising antibacterial activity, with compound 3 showing favorable binding to Bacillus subtilis laccase, E. coli DNA gyrase B, and key residues in Staphylococcus aureus. ADME-Tox predictions confirmed acceptable pharmacokinetic properties and low toxicity, notably with no significant hERG inhibition or neurotoxicity risk. Overall, compound 3 emerges as a stable and bioactive molecule with potential for further antibacterial drug development.