Advertisement

An Efficient Synthetic Method for N-Alkylcytisines

  • I. M. SakhautdinovEmail author
  • A. F. Mukhamet’yanova
  • A. G. Dosniyazova
  • V. I. Vinogradova
  • A. N. Lobov
  • M. S. Yunusov
Article

Cytisine and its derivatives are attractive to many researchers because of their broad spectra of biological activity, e.g., spasmolytic, insecticidal, cholinergic, analgesic, etc. [1, 2, 3, 4, 5, 6, 7]. Therefore, the alkaloid cytisine and its derivatives are promising compounds for possible modification and design of new medicines based on them.

Herein the development of a convenient method for alkylating cytisine at the secondary amine is communicated. Compounds 1a,b were synthesized from cytisine and nonyl iodide and dodecyl bromide by heating the mixture at 150°C for 6 h. Prolonged refluxing in various solvents (DMSO, DMF, o-xylene) formed 1a,b in yields <20% with mixtures of unidentified side products.

Notes

Acknowledgment

The work was performed under State Task Topic AAAA-A17-117011910025-6 and was financially supported by the Russian Foundation for Basic Research (Grant No. 18-53-41004) and used equipment at Khimiya Common Use Center, Ufa Institute of Chemistry, Russian Academy of Sciences.

References

  1. 1.
    L. Yu, X. Wang, Z.-F. Chen, B. Jiang, D.-Y. Shang, Y.-X. Sun, and Y.-B. Ji, Mol. Med. Rep., 16 (3), 3363 (2017).CrossRefGoogle Scholar
  2. 2.
    P. B. Tutka and W. Zatonski, Pharmacol. Rep., 58 (6), 777 (2006).Google Scholar
  3. 3.
    E. G. Perez, C. Mendez-Galvez, and B. K. Cassels, Nat. Prod. Rep., 29 (5), 555 (2012).CrossRefGoogle Scholar
  4. 4.
    S. Chacko and S. Samanta, Biomed. Pharmacother., 84, 1679 (2016).CrossRefGoogle Scholar
  5. 5.
    T. Aniszewski, Alkaloids – Secrets of Life, Elsevier, Amsterdam, 2007, 335 pp.Google Scholar
  6. 6.
    Sh. B. Rakhimov, Zh. I. Islamova, V. I. Vinogradova, Z. A. Khushbaktova, S. O. Osipova, and V. N. Syrov, Khim.-farm. Zh., 47 (4), 30 (2013).Google Scholar
  7. 7.
    D. V. Shishkin, “Synthesis of biologically active N(12)-substituted cytisines,” Candidate Dissertation, Inst. Org. Chem., Ufa Sci. Center, RAS, Ufa, 2009, 129 pp.Google Scholar
  8. 8.
    J. Rouden, M.-C. Lasne, J. Blanchet, and J. Baudoux, Chem. Rev., 114 (1), 712 (2014).CrossRefGoogle Scholar
  9. 9.
    M. S. Frasinyuk, A. V. Turov, V. I. Vinogradova, and V. P. Khilya, Chem. Nat. Compd., 43, 285 (2007).CrossRefGoogle Scholar

Copyright information

© Springer Science+Business Media, LLC, part of Springer Nature 2019

Authors and Affiliations

  • I. M. Sakhautdinov
    • 1
    Email author
  • A. F. Mukhamet’yanova
    • 1
  • A. G. Dosniyazova
    • 2
  • V. I. Vinogradova
    • 3
  • A. N. Lobov
    • 1
  • M. S. Yunusov
    • 1
  1. 1.Ufa Institute of ChemistryRussian Academy of SciencesUfaRussia
  2. 2.Bashkir State UniversityUfaRussia
  3. 3.S. Yu. Yunusov Institute of the Chemistry of Plant SubstancesAcademy of Sciences of the Republic of UzbekistanTashkentUzbekistan

Personalised recommendations