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Synthesis and neurotropic activity of new 3-(arylmethyl)aminopyridine-2(1H)-one

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Abstract

The reaction of 3-amino-6-methyl-4-phenylpyridine-2(1H)-one with aromatic aldehydes resulted in the corresponding Schiff bases, which reduction with sodium borohydride led to the formation of 3-(arylmethylamino)-6-methyl-4-phenylpyridine-2(1H)-ones. The structure of all prepared compounds was proved by 1H and 13C NMR spectroscopy. The initial evaluation of the synthesized compounds in vivo was carried out for a tranquilizing (anxiolytic) activity by «light–dark box test» and antidepressant activity by Porsolt’s «behavioral despair test». Several derivatives of 3-(arylmethylamino)-6-methyl-4-phenylpyridine-2(1H)-one with higher potential neurotropic activity than that of the comparator drugs (Mexidol and Amitriptyline) were detected.

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Acknowledgements

The study was carried out with the financial support of the Russian Foundation for Basic Research within the framework of research project No. 18-33-01143 (chemical part) and the Science Committee of the Ministry of Education and Science of the Republic of Kazakhstan under Grant No. AP05131602 (biological part). Spectrophotometric studies were performed on the basis of the Research Resource Center “Natural Resource Management and Physico-Chemical Research” Institute of Chemistry, Tyumen State University (with the financial support of the Ministry of Science and Higher Education of the Russian Federation (Contract No. 05.594.21.0019, unique identification number RFMEFI59420X0019).

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Correspondence to Zarina T. Shulgau.

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Palamarchuk, I.V., Shulgau, Z.T., Kharitonova, M.A. et al. Synthesis and neurotropic activity of new 3-(arylmethyl)aminopyridine-2(1H)-one. Chem. Pap. 75, 4729–4739 (2021). https://doi.org/10.1007/s11696-021-01696-7

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  • DOI: https://doi.org/10.1007/s11696-021-01696-7

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