Skip to main content
Log in

Synthesis of Flavonoid Derivatives of Cytisine. 3. Synthesis of 7-[2-(Cytisin-12-yl)ethoxy]isoflavones

  • Published:
Chemistry of Natural Compounds Aims and scope

The possibility of using the alkaloid cytisine to synthesize N12-cytisinylethoxy derivatives of isoflavonoids and their analogs was studied. A series of substituted 7-(N12-cytisinylethoxy)isoflavones containing chromone and cytisine fragments connected through a linker were synthesized.

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.

Similar content being viewed by others

References

  1. L.-N. Zhang, P. Cao, S.-H. Tan, W. Gu, L. Shi, and H.-L. Zhu, Eur. J. Med. Chem., 43, 1543 (2008).

    Article  PubMed  CAS  Google Scholar 

  2. E. S. C. Wu, T. E. Cole, T. A. Davidson, J. C. Blosser, A. R. Borrelli, C. R. Kinsolving, T. E. Milgate, and R. B. Parker, J. Med. Chem., 30, 788 (1987).

    Article  PubMed  CAS  Google Scholar 

  3. E. S. C. Wu, J. T. Loch III, B. H. Toder, A. R. Borrelli, D. Gawlak, L. A. Radov, and N. P. Gensmantel, J. Med. Chem., 35, 3519 (1992).

    Article  PubMed  CAS  Google Scholar 

  4. S. Wetzel, W. Wilk, S. Chammaa, B. Sperl, A. G. Roth, A. Yektaoglu, S. Renner, T. Berg, C. Arenz, A. Giannis, T. I. Oprea, D. Rauh, M. Kaiser, and H. Waldmann, Angew. Chem., Int. Ed., 49, 3666 (2010).

    Article  CAS  Google Scholar 

  5. D. K. Yadav, A. K. Gautam, J. Kureel, K. Srivastava, M. Sahai, D. Singh, N. Chattopadhyay, and R. Maurya, Bioorg. Med. Chem. Lett., 21, 677 (2011).

    Article  PubMed  CAS  Google Scholar 

  6. M. Delcanale, G. Amari, E. Armani, M. Lipreri, M. Civelli, E. Galbiati, M. Giossi, P. L. Caruso, P. Crivori, P.-A. Carrupt, and B. Testa, Helv. Chim. Acta, 84, 2417 (2001).

    Article  Google Scholar 

  7. L. Betti, M. Floridi, G. Giannaccini, F. Manetti, C. Paparelli, G. Strappaghetti, and M. Botta, Bioorg. Med. Chem., 12, 1527 (2004).

    Article  PubMed  CAS  Google Scholar 

  8. M. Bonesi, R. Tundis, B. Deguin, M. R. Loizzo, F. Menichini, F. Tillequin, and F. Menichini, Bioorg. Med. Chem. Lett., 18, 5431 (2008).

    Article  PubMed  CAS  Google Scholar 

  9. W. Loewe, S. Witzel, S. Tappmeyer, and R. Albuschat, J. Heterocycl. Chem., 41, 317 (2004).

    Article  CAS  Google Scholar 

  10. H.-Q. Li, L. Shi, Q.-S. Li, P.-G. Liu, Y. Luo, J. Zhao, and H.-L. Zhu, Bioorg. Med. Chem., 17, 6264 (2009).

    Article  PubMed  CAS  Google Scholar 

  11. K. S. Babu, T. H. Babu, P. V. Srinivas, K. H. Kishore, U. S. N. Murthy, and J. M. Rao, Bioorg. Med. Chem. Lett., 16, 221 (2006).

    Article  CAS  Google Scholar 

  12. M.-Q. Zhang, Y. Wada, F. Sato, and H. Timmerman, J. Med. Chem., 38, 2472 (1995).

    Article  PubMed  CAS  Google Scholar 

  13. J. Jin, X.-B. Wang, and L.-Y. Kong, Bioorg. Med. Chem. Lett., 21, 909 (2011).

    Article  PubMed  CAS  Google Scholar 

  14. J. C. Jaen, L. D. Wise, T. G. Heffner, T. A. Pugsley, and L. T. Meltzer, J. Med. Chem., 34, 248 (1991).

    Article  PubMed  CAS  Google Scholar 

  15. A. Rampa, A. Bisi, P. Valenti, M. Recanatini, A. Cavalli, V. Andrisano, V. Cavrini, L. Fin, A. Buriani, and P. Giusti, J. Med. Chem., 41, 3976 (1998).

    Article  PubMed  CAS  Google Scholar 

  16. S. Sepulveda-Boza, G. H. Walizei, M. C. Rezende, Y. Vasquez, C. Mascayano, and L. Mejias, Synth. Commun., 31, 1933 (2001).

    Article  CAS  Google Scholar 

  17. M. S. Frasinyuk, S. P. Bondarenko, and V. P. Khilya, Khim. Prir. Soedin., 277 (2003).

  18. H. Singh and R. Pratap, Tetrahedron Lett., 47, 8161 (2006).

    Article  CAS  Google Scholar 

  19. A. Matin, N. Gavande, M. S. Kim, N. X. Yang, N. K. Salam, J. R. Hanrahan, R. H. Roubin, and D. E. Hibbs, J. Med. Chem., 52, 6835 (2009).

    Article  PubMed  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to M. S. Frasinyuk.

Additional information

Translated from Khimiya Prirodnykh Soedinenii, No. 6, November–December, 2012, pp. 859–861.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Bondarenko, S.P., Frasinyuk, M.S., Vinogradova, V.I. et al. Synthesis of Flavonoid Derivatives of Cytisine. 3. Synthesis of 7-[2-(Cytisin-12-yl)ethoxy]isoflavones. Chem Nat Compd 48, 970–973 (2013). https://doi.org/10.1007/s10600-013-0441-3

Download citation

  • Received:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10600-013-0441-3

Keywords

Navigation