Synthesis and Biological Activity of New Hydrazones Based on N-Aminomorpholine
Nurkenov O.A. Zhautikova S.B. Khlebnikov A.I. Syzdykov A.K. Fazylov S.D. Seilkhanov T.M. Kabieva S.K. Turdybekov K.M. Mendibayeva A.Z. Zhumanazarova G.M.
August 2024Multidisciplinary Digital Publishing Institute (MDPI)
Molecules
2024#29Issue 15
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.
3-acetoxy-isoindolin-1-ones , antiviral activity , functionally substituted benzaldehydes , hydrazones , molecular modeling , N-aminomorpholine , NMR spectroscopy , o-formyl benzoic acid
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Institute of Organic Synthesis and Coal Chemistry of the Republic of Kazakhstan, Karaganda, 100008, Kazakhstan
Karaganda Industrial University, Temirtau, 101400, Kazakhstan
Karaganda Medical University, Karaganda, 100024, Kazakhstan
Kizhner Research Center, National Research Tomsk Polytechnic University, Tomsk, 634050, Russian Federation
Faculty of Chemistry, National Research Tomsk State University, Tomsk, 634050, Russian Federation
Sh. Ualikhanov Kokshetau University, Kokshetau, 020000, Kazakhstan
Karaganda Buketov University, Karaganda, 100028, Kazakhstan
Institute of Organic Synthesis and Coal Chemistry of the Republic of Kazakhstan
Karaganda Industrial University
Karaganda Medical University
Kizhner Research Center
Faculty of Chemistry
Sh. Ualikhanov Kokshetau University
Karaganda Buketov University
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