Synthesis, crystal structure, hirshfeld surface analysis, DFT calculations, anti-diabetic activity and molecular docking studies of (E)-N’-(5-bromo-2-hydroxybenzylidene) isonicotinohydrazide

Abstract In this present work, the newly synthesized compound E)-N’-(5-bromo-2-hydroxybenzylidene)isonicotinohydrazide (2) has been synthesized and characterized by IR, 1H &13C NMR, ESI-MS and single crystal X-ray diffraction analysis using experimental and theoretical methods. The molecular geometry, vibrational frequencies, frontier molecular orbital (HOMO-LUMO) energies and thermodynamic properties of the title molecule were explored using Density Functional Theory (DFT) calculation via B3LYP method with 6–31++G (d,p) basis set. Moreover, Hirshfeld and Molecular electrostatic potential (MEP) surfaces analyses were investigated. In addition, the title compound was evaluated for their in vitro antidiabetic activity against α-glucosidase and α-amylase enzymes. Finally, Molecular docking studies were performed between the title ligand and 1CLV/2ZE0 enzymes. Docking calculations showed that the 2-2ZE0 complex is more stable than 2-1CLV complex, since it has the best inhibitory impact whose their total energy score equal to −108.68 kcal/mol. Docking results reveal that the main interaction forces are H-bond and van der Waals interactions.