SYNTHESIS, SPATIAL STRUCTURE, AND NOOTROPIC ACTIVITY OF N-CYANOMETHYLANABASINE

N-cyanomethylanabasine is prepared with an yield of 70% by the interaction of the alkaloid anabasine with glyconitrile. It is shown that the highest yield of the product is achieved by conducting the reaction in aqueous or water-alcohol environments. The structure of the synthesized compound is esta...

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Bibliographic Details
Published in:Journal of structural chemistry 2022-06, Vol.63 (6), p.944-950
Main Authors: Turdybekov, K. M., Nurkenov, O. A., Seilkhanov, T. M., Fazylov, S. D., Turdybekova, Ya. G., Kudusov, A. S.
Format: Article
Language:English
Subjects:
Atomic
Atomic/Molecular Structure and Spectra
Chemistry
Chemistry and Materials Science
Crystal structure
Inorganic Chemistry
Molecular
Nitrogen
NMR spectroscopy
Optical and Plasma Physics
Physical Chemistry
Piperidine
Solid State Physics
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Summary:N-cyanomethylanabasine is prepared with an yield of 70% by the interaction of the alkaloid anabasine with glyconitrile. It is shown that the highest yield of the product is achieved by conducting the reaction in aqueous or water-alcohol environments. The structure of the synthesized compound is established by 1 H and 13 C NMR spectroscopy and by using the HMQC 2D spectroscopy data ( 1 H– 13 C). The crystal structure of N-cyanomethylanabasine is determined by XRD. It is shown that the orientation and rotation of the pyridine ring relative to the piperidine ring is determined by Van der Waals interaction with the substituent at the nitrogen atom of the piperidine ring. It is established that this compound activates predominantly type B monoamine oxidase, which indicates the presence of a nootropic effect.
ISSN:0022-4766
1573-8779
DOI:10.1134/S0022476622060117