The Synthesis, spectroscopical studies, DFT, ADMET, molecular docking analysis, antimalarial, antimicrobial activities of some E-imines and XRD structure of (E)-N-(2-bromobenzylidene)-2-(trifluoromethyl)benzenamine

Abstract

Two series of aryl E-amines was synthesised through fly-ash:Bi₂O₃-SO₄^2- catalyzed aryl amine–aldehyde condensation under ultrasound-promoted, eco-friendly solvent conditions. The reaction afforded the target compounds with an excellent yield 80%. The synthesized imines were thoroughly characterized using elemental (micro) analysis, analytical techniques, and various spectroscopic methods. The molecular structure of N-(2-bromobenzylidene)-2-(trifluoromethyl)benzenamine was unambiguously confirmed through single-crystal X-ray diffraction spectrum. Density Functional Theory (DFT) computations were utilized to explore the optimized geometries, molecular electrostatic potential maps, and frontier molecular orbitals (FMOs) of the compounds. Mulliken charge distribution analysis was also conducted to gain insight into the electronic characteristics of the imines. Additionally, ADMET predictions provided an initial evaluation of their pharmacokinetic and pharmacodynamic profiles. Molecular docking studies were conducted to investigate protein–ligand interactions, revealing potential binding affinities within a target protein. The antimicrobial efficacy of the synthesized imines was further assessed through the Bauer-Kirby disk diffusion approach against a panel of bacterial and fungal strains. In vitro studies were conducted to evaluate the antimalarial potency of these imines against P. falciparum Thai strain using a protein-targeted microbial assay system.