Synthesis, crystal structure, DFT, alpha-glucosidase and alpha-amylase inhibition and molecular docking studies of (E)- N '-(4-chlorobenzylidene)-5-phenyl-1H-pyrazole-3-carbohydrazide


Karrouchi K., Fettach S., Anouar E. H. , TÜZÜN B. , Radi S., Alharthi A. I. , ...More

JOURNAL OF MOLECULAR STRUCTURE, vol.1245, 2021 (Journal Indexed in SCI) identifier identifier

  • Publication Type: Article / Article
  • Volume: 1245
  • Publication Date: 2021
  • Doi Number: 10.1016/j.molstruc.2021.131067
  • Title of Journal : JOURNAL OF MOLECULAR STRUCTURE
  • Keywords: Pyrazole, Crystal structure, DFT calculations, alpha-glucosidase, alpha-amylase, Molecular docking, SCHIFF-BASES, PYRAZOLE, DERIVATIVES, ANTIOXIDANT, COMPLEXES, CO(II)

Abstract

In this work, a novel crystal i.e. (E)-N'-(4-chlorobenzylidene)-5-phenyl-1H-pyrazole-3-carbohydrazide has been synthesized and characterized using various spectroscopic techniques. The (E)-configuration of the azomethine (N=CH) was confirmed by single crystal X-ray analysis. The molecule crystallizes in the monoclinic space group, P21/c, a = 15.629(9) angstrom, b = 7.152(4) angstrom, c = 14.707(9) angstrom, beta = 111.061(15)degrees, V = 1534.1(6) angstrom(3) and Z = 4. In addition, the elucidated molecular structure was confirmed by comparing the predicted Z-matrix geometries and spectroscopic data with the experimental ones. DFT calculations have been carried out in gas and IEFPCM solvent at the B3LYP/6-31+G(d,p). The in vitro anti-diabetic potential of the title compound was evaluated against alpha-glucosidase and alpha-amylase enzymes. Molecular docking studies showed that the various interactions tightly anchored the title compound to the active site, which makes it a more potent alpha-glucosidase inhibitor compared to well-known Acarbose. (C) 2021 Elsevier B.V. All rights reserved.