Skip to main content
SpringerLink
Log in

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

  • Published:
Journal of Structural Chemistry Aims and scope Submit manuscript

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.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Fig. 1
Fig. 2
Fig. 3

Similar content being viewed by others

REFERENCES

  1. Yu. M. Shafran, V. A. Bakulev, and V. S. Mokrushin. Russ. Chem. Rev., 1989, 58(2), 148-162. https://doi.org/10.1070/RC1989v058n02ABEH003432

    Article  Google Scholar 

  2. E. N. Zilberman. Reaktsii nitrilov (Nitrile Reactions). Moscow: Chemistry, 1972. [In Russian]

  3. O. A. Nurkenov, A. M. Gazaliev, K. M. Turdybekov, A. B. Shalbaeva A. Aubakirova, and M. Zh. Zhurinov. Russ. J. Gen. Chem., 1999, 69(4), 675-678.

  4. A. Zh. Aubakirova, O. A. Nurkenov, A. M. Gazaliev, G. G. Baikenova, and M. Zh. Zhurinov. Russ. J. Gen. Chem., 2001, 71(1), 151/152. https://doi.org/10.1023/A:1012332929771

    Article  CAS  Google Scholar 

  5. A. M. Gazaliev, O. A. Nurkenov, and M. Zh. Zhurinov. Khimiya -aminonitrilov (Chemistry of -Aminonitriles). Almaty: Gylym, 1998. [In Russian]

  6. CrysAlis Pro. Yarnton, Oxfordshire, England: Agilent Technologies, 2014.

  7. G. M. Sheldrick. Acta Crystallogr., Sect. A, 2008, 64, 112-122. https://doi.org/10.1107/S0108767307043930

    Article  Google Scholar 

  8. G. M. Sheldrick. Acta Crystallogr., Sect. C, 2015, 71, 3-8. https://doi.org/10.1107/S2053229614024218

    Article  Google Scholar 

  9. G. Mustafina. Synthesis of N- and N,N-aminoderivatives of Nitrile Glycolic Acid and Polymers Based on Them: PhD Thesis. Karaganda: University of Karaganda, 1993.

  10. M. Wojciechowska-Nowak, W. Boczon, U. Rychlewska, and B. Warzajtis. J. Mol. Struct., 2007, 840, 44-52. https://doi.org/10.1016/j.molstruc.2006.11.037

    Article  CAS  Google Scholar 

  11. F. H. Allen, O. Kennard, D. G. Watson, L. Brammer, A. G. Orpen, and R. Taylor. J. Chem. Soc., Perkin Trans. 2, 1987, S1-S19. https://doi.org/10.1039/p298700000s1

    Article  Google Scholar 

  12. Atlas of Steroid Structure, Vol. 1 / Eds. W. L. Duax and D. A. Norton. New York: IFI/PLENUM, 1975.

  13. A. M. Gazaliev, M. Zh. Zhurunov, S. A. Dyusambaev, K. M. Turdybekov, S. V. Lindeman, A. V. Maleev, and Yu. T. Struchkov. Khim. Prir. Soedin., 1990, 500-505. [In Russian]

  14. N. K. Gusarova, A. V. Artemev, S. F. Malysheva, S. V. Fedorov, O. N. Kazheva, G. G. Alexandrov, O. A. Dyachenko, and B. A. Trofimov. Tetrahedron Lett., 2010, 51(14), 1840-1843. https://doi.org/10.1016/j.tetlet.2010.01.116

    Article  CAS  Google Scholar 

  15. A. V. Artemev, S. F. Malysheva, N. K. Gusarova, N. A. Belogorlova, S. V. Fedorov, B. V. Timokhin, V. I. Smirnov, and B. A. Trofimov. Chem. Heterocycl. Compd., 2012, 48(3), 448-452. https://doi.org/10.1007/s10593-012-1013-3

    Article  CAS  Google Scholar 

  16. M. K. Ibraev, D. M. Turdybekov, A. T. Takibaeva, O. A. Nurkenov, K. M. Turdybekov, A. M. Gazaliev, and S. M. Adekenovim. Russ. J. Gen. Chem., 2006, 76(4), 638-640. https://doi.org/10.1134/S1070363206040232

    Article  CAS  Google Scholar 

  17. I. V. Kulakov, O. A. Nurkenov, D. M. Turdybekov, B. T. Ibragimov, S. A. Talipov, Z. M. Zhambekov, A. A. Ainabaev, and K. M. Turdybekov. Chem. Nat. Compd., 2009, 45(2), 209-212. https://doi.org/10.1007/s10600-009-9284-3

    Article  CAS  Google Scholar 

  18. I. V. Kulakov, O. A. Nurkenov, D. M. Turdybekov, and K. M. Turdybekov. Chem. Nat. Compd., 2010, 46(2), 257-261. https://doi.org/10.1007/s10600-010-9582-9

    Article  CAS  Google Scholar 

  19. O. A. Nurkenov, Zh. B. Satpaeva, S. D. Fazylov, T. M. Seilkhanov, K. M. Turdybekov, D. M. Turdybekov, S. B. Akhmetova, A. S. Makhmutova, and A. M. Gazaliev. Chem. Nat. Compd., 2016, 52(2), 276-279. https://doi.org/10.1007/s10600-016-1613-8

    Article  CAS  Google Scholar 

  20. O. A. Nurkenov, Zh. S. Nurmaganbetova, T. M. Seilkhanov, S. D. Fazylov, Zh. B. Satpayeva, K. M. Turdybekov, S. A. Talipov, and R. B. Seydakhmetova. Russ. J. Gen. Chem., 2019, 89(10), 2044-2051. https://doi.org/10.1134/S1070363219100098

    Article  CAS  Google Scholar 

  21. K. M. Turdybekov. Stereochemistry of Some Structural Types of Alkaloids and Sesquiterpenoids: Doctoral (Chem.) Thesis. Karaganda: University of Karaganda, 1998.

  22. Yu. V. Zefirov and P. M. Zorkii. J. Struct. Chem., 1974, 15(1), 102-105. https://doi.org/10.1007/BF00753791

    Article  Google Scholar 

Download references

Funding

This work was funded by the Science Committee of the Ministry of Education and Science of the Republic of Kazakhstan (No. BR10965230).

Author information

Authors and Affiliations

  1. Karaganda Buketov University, Karaganda, Republic of Kazakhstan

    K. M. Turdybekov & A. S. Kudusov

  2. Institute of Organic Synthesis and Coal Chemistry, Karaganda, Republic of Kazakhstan

    O. A. Nurkenov & S. D. Fazylov

  3. Ualikhanov Kokshetau University, Kokshetau, Republic of Kazakhstan

    T. M. Seilkhanov

  4. Karaganda Medical University, Karaganda, Republic of Kazakhstan

    Ya. G. Turdybekova

Authors
  1. K. M. Turdybekov
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. O. A. Nurkenov
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. T. M. Seilkhanov
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. S. D. Fazylov
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. Ya. G. Turdybekova
    View author publications

    You can also search for this author in PubMed Google Scholar

  6. A. S. Kudusov
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to K. M. Turdybekov.

Ethics declarations

The authors declare that they have no conflicts of interests.

Additional information

Russian Text © The Author(s), 2022, published in Zhurnal Strukturnoi Khimii, 2022, Vol. 63, No. 6, pp. 810-817.https://doi.org/10.26902/JSC_id93851

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Turdybekov, K.M., Nurkenov, O.A., Seilkhanov, T.M. et al. SYNTHESIS, SPATIAL STRUCTURE, AND NOOTROPIC ACTIVITY OF N-CYANOMETHYLANABASINE. J Struct Chem 63, 944–950 (2022). https://doi.org/10.1134/S0022476622060117

Download citation

  • Received:

  • Revised:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1134/S0022476622060117

Keywords

Search

Navigation