Molecules (Jul 2024)

Synthesis and Biological Activity of New Hydrazones Based on N-Aminomorpholine

  • Oralgazy A. Nurkenov,
  • Saule B. Zhautikova,
  • Andrei I. Khlebnikov,
  • Ardak K. Syzdykov,
  • Serik D. Fazylov,
  • Tulegen M. Seilkhanov,
  • Saule K. Kabieva,
  • Kobylandy M. Turdybekov,
  • Anel Z. Mendibayeva,
  • Gaziza M. Zhumanazarova

DOI
https://doi.org/10.3390/molecules29153606
Journal volume & issue
Vol. 29, no. 15
p. 3606

Abstract

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The data on the synthesis of N-aminomorpholine hydrazones are presented. It is shown that the interaction of N-aminomorpholine with functionally substituted benzaldehydes and 4-pyridinaldehyde in isopropyl alcohol leads to the formation of corresponding hydrazones. The structure of the synthesized compounds was studied by 1H and 13C NMR spectroscopy methods, including the COSY (1H-1H), HMQC (1H-13C) and HMBC (1H-13C) methodologies. The values of chemical shifts, multiplicity, and integral intensity of 1H and 13C signals in one-dimensional NMR spectra were determined. The COSY (1H-1H), HMQC (1H-13C), and HMBC (1H-13C) results revealed homo- and heteronuclear interactions, confirming the structure of the studied compounds. The antiviral, cytotoxic, and antimicrobial activity of some synthesized hydrazones were investigated. It is shown that 2-((morpholinoimino)methyl)benzoic acid has a pronounced viral inhibitory property, comparable in its activity to commercial drugs Tamiflu and Remantadine. A docking study was performed using the influenza virus protein models (1930 Swine H1 Hemagglutinin and Neuraminidase of 1918 H1N1 strain). The potential binding sites that are complementary with 2-((morpholinoimino)methyl)benzoic acid were found.

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