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

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 act...

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Bibliographic Details
Published in:Chemistry of natural compounds 2018-03, Vol.54 (2), p.315-323
Main Authors: Spivak, A. Yu, Galimshina, Z. R., Nedopekina, D. A., Odinokov, V. N.
Format: Article
Language:English
Subjects:
Analogs
Chemical synthesis
Cycloaddition
Cytotoxicity
Medicine
Organic Chemistry
Pharmacy
Plant Sciences
Saponins
Triazoles
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Summary: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.
ISSN:0009-3130
1573-8388
DOI:10.1007/s10600-018-2331-1