Please use this identifier to cite or link to this item: http://hdl.handle.net/10553/50555
Title: 'Click' synthesis of triazole-based spirostan saponin analogs
Authors: Pérez-Labrada, Karell
Brouard Martín,Ignacio 
Morera, Cercis
Estevez, Francisco 
Bermejo, Jaime
Rivera, Daniel G.
UNESCO Clasification: 32 Ciencias médicas
3209 Farmacología
Keywords: Steroids
Carbohydrates
Saponins
Click chemistry
Cycloaddition reactions
Issue Date: 2011
Project: Evaluación de Potenciales Compuestos Antileucémicos. 
Journal: Tetrahedron 
Abstract: Novel analogs of spirostan saponins in which the glycosidic bond has been replaced by a triazole linkage are described. For this, a direct oligosaccharide-steroid conjugation approach based on the Cu-1-catalyzed azide-alkyne 1,3-dipolar cycloaddition was implemented, leading to diverse combinations of saponin analogs with variations in the trisaccharide moiety, the artificial linkage, and the steroid-skeleton functionalization. This 'click' process proved great efficiency for the ligation of two bulky building blocks (e.g., chacotriose derivatives and spirostanes bearing axial azides), which enabled the rapid creation of a small library of triazole-based analogs for cytotoxicity evaluation. A molecular modeling study was performed to understand the conformational and electronic differences between a natural saponin and its triazole-based analogs.
URI: http://hdl.handle.net/10553/50555
ISSN: 0040-4020
DOI: 10.1016/j.tet.2011.08.003
Source: Tetrahedron[ISSN 0040-4020],v. 67 (40), p. 7713-7727 (Octubre 2011)
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