Skip to main content
Log in

Bromination of Triacanthine

  • Published:
Chemistry of Natural Compounds Aims and scope

Bromination of the purine alkaloid triacanthine by N-bromosuccinimide in CHCl3, AcOH, and various alcohols was studied. The new derivatives 8-bromo-, 12,13-dibromo-, 8,12-dibromo-13-hydroxymethyl-, hydroxyethyl-, hydroxypropyl-, and hydroxybutyltriacanthine were prepared. The structures of the prepared compounds were proven using 1H and 13C NMR spectral data and X-ray crystal structure analyses.

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.

Scheme 1.
Fig. 1.

Similar content being viewed by others

References

  1. I. Saikia, A. J. Borah, and P. Phukan, Chem. Rev., 116, 6837 (2016).

    Article  CAS  PubMed  Google Scholar 

  2. P. A. Ramazanova, A. V. Tarakanova, M. V. Vagabov, V. V. Litvinova, and A. V. Anisimov, Chem. Heterocycl. Compd., 36, 201 (2000).

    Article  CAS  Google Scholar 

  3. N. Yu. Slivka, Yu. I. Gevaza, and V. I. Staninets, Chem. Heterocycl. Compd., 40 (5), 660 (2004).

    Article  CAS  Google Scholar 

  4. G. Kim, N. M. Sudolova, P. A. Slepuhin, and V. N. Charushin, Chem. Heterocycl. Compd., 46 (11), 1420 (2010).

    Article  Google Scholar 

  5. E. S. Il′inykh and D. G. Kim, Chem. Heterocycl. Compd., 47 (5), 636 (2011).

    Article  Google Scholar 

  6. E. A. Vershinina, Russ. Chem. Bull., 70 (2), 391 (2021).

    Article  CAS  Google Scholar 

  7. L. V. Gyulbudagyan, I. L. Aleksanyan, and A. A. Avetisyan, Arm. Khim. Zh., 636 (1989).

  8. A. U. Ubaidullaev, V. I. Vinogradova, Sh. N. Zhurakulov, N. I. Mukarramov, Kh. M. Bobakulov, K. A. Turgunov, and B. Tashkhodzhaev, Chem. Nat. Compd., 58, 1101 (2022).

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  9. S.-S. Shin, Y.-J. Park, B. Hwang, S. L. Park, S.-W. Han, S.-S. Park, Y. H. Choi, W.-J. Kim, and S.-K. Moon, Phytomedicine, 64, 153069 (2019).

    Article  CAS  PubMed  Google Scholar 

  10. Sh. B. Rakhimov, V. I. Vinogradova, K. K. Turgunov, B. Tashkhodzhaev, and M. G. Levkovich, Chem. Nat. Compd., 59, 743 (2023).

    Article  CAS  Google Scholar 

  11. F. N. Allen, O. Kennard, D. G. Watson, L. Brammer, A. G. Orpen, and R. Taylor, J. Chem. Soc., Perkin Trans. II, S1 (1987).

  12. L. Krause, R. Herbs-Irmer, G. M. Sheldrick, and D. Stalke, J. Appl. Crystallogr., 48, 3 (2015).

    Article  CAS  PubMed  PubMed Central  Google Scholar 

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

  14. G. M. Sheldrick, Acta Crystallogr., Sect. C: Struct. Chem., 71, 3 (2015).

Download references

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to Sh. B. Rakhimov.

Additional information

Translated from Khimiya Prirodnykh Soedinenii, No. 5, September–October, 2023, pp. 747–751.

Rights and permissions

Springer Nature or its licensor (e.g. a society or other partner) holds exclusive rights to this article under a publishing agreement with the author(s) or other rightsholder(s); author self-archiving of the accepted manuscript version of this article is solely governed by the terms of such publishing agreement and applicable law.

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Rakhimov, S.B., Vinogradova, V.I., Turgunov, K.K. et al. Bromination of Triacanthine. Chem Nat Compd 59, 886–890 (2023). https://doi.org/10.1007/s10600-023-04141-1

Download citation

  • Received:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10600-023-04141-1

Keywords

Navigation