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This is an early access version, the complete PDF, HTML, and XML versions will be available soon.
Article

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

by
Oralgazy A. Nurkenov
1,2,
Saule B. Zhautikova
3,*,
Andrei I. Khlebnikov
4,5,
Ardak K. Syzdykov
1,2,
Serik D. Fazylov
1,
Tulegen M. Seilkhanov
6,
Saule K. Kabieva
2,
Kobylandy M. Turdybekov
7,
Anel Z. Mendibayeva
1,2 and
Gaziza M. Zhumanazarova
2,*
1
Institute of Organic Synthesis and Coal Chemistry of the Republic of Kazakhstan, Karaganda 100008, Kazakhstan
2
Karaganda Industrial University, Temirtau 101400, Kazakhstan
3
Karaganda Medical University, Karaganda 100024, Kazakhstan
4
Kizhner Research Center, National Research Tomsk Polytechnic University, Tomsk 634050, Russia
5
Faculty of Chemistry, National Research Tomsk State University, Tomsk 634050, Russia
6
Sh. Ualikhanov Kokshetau University, Kokshetau 020000, Kazakhstan
7
Karaganda Buketov University, Karaganda 100028, Kazakhstan
*
Authors to whom correspondence should be addressed.
Molecules 2024, 29(15), 3606; https://doi.org/10.3390/molecules29153606
Submission received: 2 July 2024 / Revised: 22 July 2024 / Accepted: 23 July 2024 / Published: 30 July 2024
Versions Notes

Abstract

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.
Keywords: N-aminomorpholine; hydrazones; functionally substituted benzaldehydes; o-formyl benzoic acid; 3-acetoxy-isoindolin-1-ones; NMR spectroscopy; antiviral activity; molecular modeling N-aminomorpholine; hydrazones; functionally substituted benzaldehydes; o-formyl benzoic acid; 3-acetoxy-isoindolin-1-ones; NMR spectroscopy; antiviral activity; molecular modeling

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MDPI and ACS Style

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. Synthesis and Biological Activity of New Hydrazones Based on N-Aminomorpholine. Molecules 2024, 29, 3606. https://doi.org/10.3390/molecules29153606

AMA Style

Nurkenov OA, Zhautikova SB, Khlebnikov AI, Syzdykov AK, Fazylov SD, Seilkhanov TM, Kabieva SK, Turdybekov KM, Mendibayeva AZ, Zhumanazarova GM. Synthesis and Biological Activity of New Hydrazones Based on N-Aminomorpholine. Molecules. 2024; 29(15):3606. https://doi.org/10.3390/molecules29153606

Chicago/Turabian Style

Nurkenov, Oralgazy A., Saule B. Zhautikova, Andrei I. Khlebnikov, Ardak K. Syzdykov, Serik D. Fazylov, Tulegen M. Seilkhanov, Saule K. Kabieva, Kobylandy M. Turdybekov, Anel Z. Mendibayeva, and Gaziza M. Zhumanazarova. 2024. "Synthesis and Biological Activity of New Hydrazones Based on N-Aminomorpholine" Molecules 29, no. 15: 3606. https://doi.org/10.3390/molecules29153606

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