Synthesis, crystal structure, spectroscopic characterization, DFT calculations, Hirshfeld surface analysis, biological activity studies, molecular docking investigation, and ADMET properties evaluation of a novel 3-substituted coumarin derivative

In this paper, the title compound was synthesized by nucleophilic substitution and Schiff base reaction from 4Hydroxycoumarin as the starting material. 2-({1-[(3E)-2,4-dioxo-3,4-dihydro-2H-chromen-3-ylidene]ethyl} amino)benzoic acid was designed and synthesized, and the structure was characterized by spectroscopic techniques including UV-vis, FT-IR, 1H NMR, 13C NMR and MS. The single crystal structure of the target molecule was confirmed by X-ray diffraction and showed intermolecular O-H...O, C-H...O hydrogen bonding which was the most important factor in the crystal stacking interaction. The geometrical parameters, molecular electrostatic potential (MEP), and frontier molecular orbital analysis (FMOs) of the molecule are also presented to reveal the physicochemical properties of the investigated compound. In addition, Hirshfeld surface analysis of the title molecule by using crystal information file, a significant contribution (33.6%) to the crystal packing comes from O...H/H...O contacts. Molecular docking study showed that compound has significant binding affinity (Delta G = -54.98 kcal/mol). Additionally, the title compound exhibited MIC values of 4.04, 32.33, and 8.08 mu g & sdot;mL- 1 against S. parauberis, S.aureus, L.garvieae, and E.piscicida, respectively. The results presented herein demonstrate the compound's remarkable efficacy in effectively inhibiting bacterial growth, thereby providing a valuable reference for the biosynthesis of coumarin derivatives and facilitating further exploration of their medicinal potential.