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

Turdybekov K.M. Nurkenov O.A. Seilkhanov T.M. Fazylov S.D. Turdybekova Y.G. Kudusov A.S.
June 2022 Pleiades journals

Journal of Structural Chemistry
2022 #63 Issue 6 944 - 950 pp.

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. [Figure not available: see fulltext.]

alkaloid anabasine , glyconitrile , N-cyanomethylanabasine , NMR spectroscopy , X-ray diffraction analysis , α-aminonitrile

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Karaganda Buketov University, Karaganda, Kazakhstan
Institute of Organic Synthesis and Coal Chemistry, Karaganda, Kazakhstan
Ualikhanov Kokshetau University, Kokshetau, Kazakhstan
Karaganda Medical University, Karaganda, Kazakhstan

Karaganda Buketov University
Institute of Organic Synthesis and Coal Chemistry
Ualikhanov Kokshetau University
Karaganda Medical University

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