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