Synthesis, crystal structure, spectroscopic characterization, alpha-glucosidase inhibition and computational studies of (E)-5-methyl- N '-(pyridin-2-ylmethylene)-1H-pyrazole-3-carbohydrazide


Karrouchi K., Fettach S., Tamer O., AVCI D., BAŞOĞLU A., ATALAY Y., ...More

JOURNAL OF MOLECULAR STRUCTURE, vol.1248, 2022 (Journal Indexed in SCI) identifier identifier

  • Publication Type: Article / Article
  • Volume: 1248
  • Publication Date: 2022
  • Doi Number: 10.1016/j.molstruc.2021.131506
  • Title of Journal : JOURNAL OF MOLECULAR STRUCTURE
  • Keywords: Pyrazole, Crystal structure, DFT, alpha-glucosidase inhibition, Docking, NONLINEAR-OPTICAL PROPERTIES, DFT CALCULATIONS, SCHIFF-BASES, COMPLEXES, CU(II), ACID, ANTIOXIDANT, DERIVATIVES, ENERGIES, DOCKING

Abstract

A new crystal, i.e, (E)-5-methyl-N'-(pyridin-2-ylmethylene)-1H-pyrazole-3-carbohydrazide (E-MPPC) has been synthesized and characterized by using FT-IR, UV-Vis, H-1-NMR, C-13-NMR, ESI-MS and single-crystal X-ray diffraction. In addition, a density functional theory study for the title compound was carried out. The theoretical geometry of the ground state and the electronic structure of the title compound were optimized by the DFT/B3LYP method in conjunction with 6-311++G(d,p) basis set. E-MPPC was evaluated in vitro for their alpha-glucosidase enzyme inhibition. The title compound displayed moderate inhibitory activity with IC50 value of 714.25 +/- 8.33 mu M against alpha-glucosidase enzyme. In addition, molecular docking study was performed to investigate how E-MPPC interacts with the protein structure of alpha-glucosidase enzyme. Final intermolecular energy and estimated inhibition constant for this docking study were obtained as -5.50 kcal/mol and 173.57 mu M, respectively. The first order static hyperpolarizability (beta) parameter for E-MPPC was also calculated as 11.2 x 10(-30) esu. Natural bond orbital analysis was also executed to investigate intramolecular charge transfer interactions in the title compound. (C) 2021 Elsevier B.V. All rights reserved.