Skip to main content
SpringerLink
Log in

Synthesis of berberine bromide analogs containing tertiary amides of acetic acid in the 9-O-position

  • Published:
Chemistry of Natural Compounds Aims and scope

9-O-Acetamide analogs of berberine bromide were prepared in 20–87% yields via reaction of the isoquinoline alkaloid berberrubine with tertiary amides of bromoacetic acid. Aminolysis did not occur during reaction of methyl-2-(9-demethoxyberberine bromide-9-yl)hydroxyacetate with secondary amines. The corresponding acid or its ethyl ester was isolated.

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

Similar content being viewed by others

References

  1. W. Kong, J. Wei, P. Abidi, M. Lin, S. Inaba, C. Li, Y. Wang, Z. Wang, S. Sil, H. Pan, Sh. Wang, J. Wu, Y. Wang, Z. Li, J. Liu, and J.-D. Jiang, Nat. Med., 10, 1344 (2004); W. J. Kong, J. Liu, and J. D. Jiang, J. Mol. Med., 84, 29 (2006).

  2. J. M. Beale and J. H. Block, eds., Wilson and Gisvold’s Textbook of Organic Medicinal and Pharmaceutical Chemistry, 12th Ed., Wolters Kluwer, Lippincott Williams & Wilkins, Philadelphia, 2011.

  3. K. Iwasa and M. Kamigauchi, Phytochemistry, 41 (6), 1511 (1996).

    Article  CAS  Google Scholar 

  4. Yu. D. Sadykov, S. B. Davidyants, K. T. Poroshin, I. N. Grigina, Dokl. Akad. Nauk Tadzh. SSR, 10 (2), 18 (1967).

    CAS  Google Scholar 

  5. G. Frerichs and P. Stoepel, Arch. Pharm., 251, 321 (1913).

    Article  Google Scholar 

  6. H. Liu, J. Wang, R. Zhang, N. Cairns, and J. Liu, Pat. WO2009002873; Chem. Abstr., 150, 98173 (2009).

  7. I. L. Kotlyarevskii and L. A. Mal’kova, Izv. Akad. Nauk SSSR, Ser. Khim., 11, 2613 (1972).

    Google Scholar 

  8. K. Amin and K. Granberg, Pat. WO2007008145; Chem. Abstr., 146, 163138 (2007); T. Suzuki, A. Matsuura, A. Kouketsu, Sh. Hisakawa, H. Nakagawa, and N. Miyata, Bioorg. Med. Chem., 13 (13), 4332 (2005); G. Viti, R. Nannicini, R. Ricci, V. Pestellini, L. Abelli, and M. Furio, Eur. J. Med. Chem., 29 (5), 401 (1994).

  9. L. Huang, Z. Luo, F. He, J. Lu, and X. Li, Bioorg. Med. Chem., 18 (12), 4475 (2010).

    Article  PubMed  CAS  Google Scholar 

  10. H. Jiang, K. Ding, X. Wang, L. Huang, Z. Luo, T. Su, and X. Li, Bioorg. Med. Chem., 19 (23), 7228 (2011).

    Article  PubMed  CAS  Google Scholar 

  11. L. Grycova, D. Hulova, L. Maier, S. Standara, M. Necas, F. Lemiere, R. Kares, J. Dostal, and R. Marek, Magn. Reson. Chem., 46, 1127 (2008).

    Article  PubMed  CAS  Google Scholar 

  12. K. Umemoto and K. Ouchi, J. Chem. Sci., 94 (1), 1 (1985).

    Article  CAS  Google Scholar 

  13. H.-O. Kalinowsky, S. Berger, and S. Brawn, 13-C NMR Spectroscopy, Wiley, New York, 1988, pp. 198–219.

  14. Brutto Formula Searcher, AlgorithmSoft, URL: http://www.algorithmsoft.com/brutto_formula_searcher/index.html

  15. I. V. Nechepurenko, M. P. Polovinka, N. I. Komarova, N. F. Salakhutdinov, and G. A. Tolstikov, RF Pat. RU2423992; Chem. Abstr., 155, 173296 (2011).

    Google Scholar 

  16. W. E. Weaver and W. M. Whaley, J. Am. Chem. Soc., 69, 515 (1947).

    Article  PubMed  CAS  Google Scholar 

  17. H. I. Kong, J. E. Crichton, and J. M. Manthorpe, Tetrahedron Lett., 52 (29), 3714 (2011) (suppl. info.); A. Cappelli, G. Bini, S. Valenti, G. Giuliani, M. Paolino, M. Anzini, S. Vomero, G. Giorgi, A. Giordani, L. P. Stasi, F. Makovec, C. Ghelardini, L. Di Cesare Mannelli, A. Concas, P. Porcu, and G. Biggio, J. Med. Chem., 54 (20), 7165 (2011) (suppl. info.); P. S.-W. Leung, Y. Teng, and P. H. Toy, Org. Lett., 12 (21), 4996 (2010) (suppl. info.); L. A. McAllister, K. L. Turner, S. Brand, M. Stefaniak, and D. J. Procter, J. Org. Chem., 71 (17), 6497 (2006).

Download references

Acknowledgment

The work was supported financially by the RAS Presidium Basic Research Program “Basic Sciences – Medicine,” Grant No. 34.

Author information

Authors and Affiliations

  1. N. N. Vorozhtsov Novosibirsk Institute of Organic Chemistry, Siberian Branch, Russian Academy of Sciences, 630090, Novosibirsk, Prosp. Akad. Lavrent’eva, 9, Russia

    I. V. Nechepurenko, N. I. Komarova, V. G. Vasil’ev & N. F. Salakhutdinov

Authors
  1. I. V. Nechepurenko
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. N. I. Komarova
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. V. G. Vasil’ev
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. N. F. Salakhutdinov
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to I. V. Nechepurenko.

Additional information

Translated from Khimiya Prirodnykh Soedinenii, No. 6, November–December, 2012, pp. 924–929.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Nechepurenko, I.V., Komarova, N.I., Vasil’ev, V.G. et al. Synthesis of berberine bromide analogs containing tertiary amides of acetic acid in the 9-O-position. Chem Nat Compd 48, 1047–1053 (2013). https://doi.org/10.1007/s10600-013-0461-z

Download citation

  • Received:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10600-013-0461-z

Keywords

Search

Navigation