Skip to main content
Log in

3-Formyl- and 3-Bromo-N-Methylcytisine Derivatives

  • Published:
Chemistry of Natural Compounds Aims and scope

    We’re sorry, something doesn't seem to be working properly.

    Please try refreshing the page. If that doesn't work, please contact support so we can address the problem.

3-Formyl- and 3-bromo-N-methylcytisine derivatives of the alkaloid N-methylcytisine from Thermopsis alterniflora were synthesized. Their structures were established using NMR spectroscopy and X-ray crystal structure analyses. The crystal structure of 3-formyl-N-methylcytisine perchlorate involves two protonated cations mutually bonded by a bifurcated N–H…O H-bond. A Br…O donor–acceptor interaction is observed in the crystal of 3-bromo-N-methylcytisine.

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

Access this article

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

Instant access to the full article PDF.

Fig. 1.

Similar content being viewed by others

References

  1. M. D. Mashkovskii, Drugs [in Russian], Novaya Volna, Moscow, 2012, 1216 pp.

    Google Scholar 

  2. M. G. Levkovich and Sh. B. Rakhimov, in: Proceedings of the Scientific Conference “Critical Problems in the Chemistry of Natural Compounds” [in Russian], Tashkent, 2009, p. 382.

  3. A. A. Freer, D. J. Robins, and G. M. Sheldrake, Acta Crystallogr., Sect. C: Cryst. Struct. Commun., 43, 1119 (1987).

  4. P. Mascagni, M. Christodoulou, W. A. Gibbons, K. Asres, J. D. Phillipson, N. Niccolai, and S. Mangani, J. Chem. Soc., Perkin Trans. 2, 9, 1159 (1987).

    Article  Google Scholar 

  5. R. B. Barlow and O. Johnson, Br. J. Pharmacol., 98, 799 (1989).

    Article  PubMed  PubMed Central  CAS  Google Scholar 

  6. T. V. Khakimova, O. A. Pukhlyakova, G. A. Shavaleeva, A. A. Fatykhov, E. V. Vasil’eva, and L. V. Spirikhin, Chem. Nat. Compd., 37, 356 (2001).

    Article  CAS  Google Scholar 

  7. K. A. Krasnov, V. G. Kartsev, A. S. Gorovoi, and V. N. Khrustalev, Chem. Nat. Compd., 38, 450 (2002).

    Article  CAS  Google Scholar 

  8. O. A. Nurkenov, A. M. Gazaliev, K. M. Turdybekov, A. B. Shalbaeva, A. Aubakirova, and M. Z. Zhurinov, Zh. Obshch. Khim., 69, 675 (1999).

    Google Scholar 

  9. J. Rouden, M. Lasne, J. Blanchet, and J. Baudoux, Chem. Rev., 114, 712 (2014).

    Article  PubMed  CAS  Google Scholar 

  10. A. Przybyl and M. Kubicki, J. Chem. Crystallogr., 42, 685 (2012).

    Article  CAS  Google Scholar 

  11. K. Yu. Suponitsky, A. V. Koval’skaya, and I. P. Tsypysheva, Chem. Nat. Compd., 50, 581 (2014).

    Article  CAS  Google Scholar 

  12. F. H. Allen, O. Kennard, D. G. Watson, L. Brammer, G. Orpen, and R. Taylor, J. Chem. Soc., Perkin Trans. 2, S1 (1987).

  13. H. Li, Y. Lu, W. Wu, and Y. Liu, Phys. Chem. Chem. Phys., 15, 4405 (2013).

    Article  PubMed  CAS  Google Scholar 

  14. K. E. Riley, J. S. Murray, P. Politzer, M. C. Concha, and P. Hobza, J. Chem. Theory Comput., 5, 155 (2009).

    Article  PubMed  CAS  Google Scholar 

  15. A. Priimagi, G. Cavallo, P. Metrangolo, and G. Resnati, Acc. Chem Res., 46, 2686 (2013).

    Article  PubMed  PubMed Central  CAS  Google Scholar 

  16. Sh. B. Rakhimov, V. I. Vinogradova, and M. G. Levkovich, Chem. Nat. Compd., 52, 874 (2016).

    Article  CAS  Google Scholar 

  17. Oxford Diffraction, CrysAlisPro, 2007, Oxford Diffraction Ltd., Abingdon, Oxfordshire, England.

  18. G. M. Sheldrick, Acta Crystallogr., Sect. A: Found. Crystallogr., 64, 112 (2008).

Download references

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to U. S. Makhmudov.

Additional information

Translated from Khimiya Prirodnykh Soedinenii, No. 4, July–August, 2018, pp. 621–623.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Makhmudov, U.S., Rakhimov, S.B., Vinogradova, V.I. et al. 3-Formyl- and 3-Bromo-N-Methylcytisine Derivatives. Chem Nat Compd 54, 735–738 (2018). https://doi.org/10.1007/s10600-018-2458-0

Download citation

  • Received:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10600-018-2458-0

Keywords

Navigation