Synthesis, Crystal Structure, Hirshfeld, DFT, Quorum Sensing Inhibition and Molecular Docking Studies of N'-{(E)-[3-(3,5-Difluorophenyl)1H-pyrazol-4-yl]methylidene}-4-methoxybenzohydrazide

Abstract

In present study, the synthesis, structural, quorum sensing inhibition and computational studies of a new N’-{(E)-[3-(3,5-difluorophenyl)-1H-pyrazol-4-yl]methylidene}-4-methoxybenzohydrazide are reported. The structure of the synthesized compound was confirmed by IR, 1H & 13C NMR and mass spectral data. The single crystals of the compound was obtained using ethanol as a crystallization solvent. The synthesized compound (C40H40N8O6F4) crystallizes in the monoclinic crystal system, C2/c space group. Various intermolecular interactions were quantified using a 3D molecular Hirshfeld surface computational method. The 2D fingerprint plots revealed that the H···H (35.9%) interactions have a major contribution to the total molecular surface. DFT studies was performed to establish the molecular crystal structure of the compound and to study the HOMO-LUMO energies of the compound. The anti-quorum sensing study of the target compound on Chromobacterium violaceum (wild type) biosensor revealed that quorum quenching activity at 300 μg/mL. Interestingly, quantitative assay exhibited more than 80% of quorum sensing inhibition without interfering cell growth (p < 0.05). Molecular docking studies of the compound on CviR protein (PDB: 3QP8) confirmed the observed activity through strong hydrogen bonding interaction with the amino acids in the binding pocket.