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

2022

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DOI 10.1134/s0022476622060117
Data confidence 70 medium
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Abstract

Abstract 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 1H and 13C NMR spectroscopy and by using the HMQC 2D spectroscopy data (1H–13C). 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.