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

Karrouchi, Khalid;Fettach, Saad;Anouar, El Hassane;Tüzün, Burak;Garcia, Yann;et.al.
(2021) Journal of Molecular Structure — Vol. 1245, n° 1245, p. 131067 (2021)

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Authors
  • Karrouchi, Khalid
    Author
  • Fettach, Saad
    Author
  • Anouar, El Hassane
    Author
  • Tüzün, Burak
    Author
  • Radi, SmaailUCLouvain
    Author
  • Garcia, YannUCLouvain
    Author
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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 (Ndouble bondCH) was confirmed by single crystal X-ray analysis. The molecule crystallizes in the monoclinic space group, P21/c, a = 15.629(9) Å, b = 7.152(4) Å, c = 14.707(9) Å, β = 111.061(15)°, V = 1534.1(6) Å3 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 α-glucosidase and α-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 α-glucosidase inhibitor compared to well-known Acarbose.
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Karrouchi, K., Fettach, S., Anouar, E. H., Tüzün, B., Radi, S., Alharthi, A. I., Ghabbour, H. A., Mabkhot, Y. N., Faouzi, M. E. A., Ansar, M., & Garcia, Y. (2021). Synthesis, crystal structure, DFT, α-glucosidase and α-amylase inhibition and molecular docking studies of (E)-N’-(4-chlorobenzylidene)-5-phenyl-1H-pyrazole-3-carbohydrazide. Journal of Molecular Structure, 1245(1245), 131067. https://doi.org/10.1016/j.molstruc.2021.131067 (Original work published 2021)