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Chemistry of Natural Compounds

, Volume 54, Issue 2, pp 315–323 | Cite as

Synthesis of New C-2 Triazole-Linked Analogs of Triterpenoid Pentacyclic Saponins

  • A. Yu. Spivak
  • Z. R. Galimshina
  • D. A. Nedopekina
  • V. N. Odinokov
Article
  • 60 Downloads

C-2 mono- and bis-1,2,3-triazole-linked analogs of lupane, ursane, and oleane triterpenoid saponins were synthesized for the first time using regioselective Cu(I)-catalyzed 1,3-dipolar cycloaddition (CuAAC) of peracetylated sugar azides and C-2 propynyl derivatives of triterpene acids. Cytotoxic activity of the synthesized compounds was studied in vitro at the National Cancer Institute (USA). Several of the synthesized compounds exhibited weak cytotoxic activity.

Keywords

triterpenoids betulinic acid ursolic acid oleanolic acid glycosides 1,2,3-triazoles 1,3-dipolar cycloaddition 

Notes

Acknowledgment

The work was financially supported by the Russian Science Foundation (Grant No. 16-13-10051). Bis-triazole derivatives 22 and 23 were synthesized by D. A. Nedopekina with financial support from the Russian Foundation for Basic Research (Grant No. mol_a 16-33-00044). We thank the National Cancer Institute (NCI) for in vitro tests for antitumor activity of the synthesized compounds.

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Copyright information

© Springer Science+Business Media, LLC, part of Springer Nature 2018

Authors and Affiliations

  • A. Yu. Spivak
    • 1
  • Z. R. Galimshina
    • 1
  • D. A. Nedopekina
    • 1
  • V. N. Odinokov
    • 1
  1. 1.Institute of Petrochemistry and CatalysisRussian Academy of SciencesUfaRussia

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