Click glycosyl triazoles

Glycosyl triazole-linked 18P-glycyrrhetinic acids were developed by clicking per-O-acetylated glycosyl azides with propargyl ester of 18P-glycyrrhetinic acid (Figure 6.3). Subsequent de-O-acetylation of these molecules afforded potential... 

Keywords Glycosjd azides - Glycosjdamines Glycosyl enamines - Glycosyl heterocycles Triazoles Click chemistry... 

In an effort to expand the click chemistry concept, Ijsselstijn et al. [43] have reported the use of two N-protected ynamides (60) as dienophiles in the Cu(I)-catalyzed cycloaddition reaction with a variety of azides, including glycosyl azides (Scheme 12). The ynamides were successfully clicked under the standard conditions for these reactions [Cu(OAc)2/Na-ascorbate] giving rise to 1-substituted 4-amino 1,2,3-triazole-Iinked sugars (61). These results are noteworthy as they allow direct access to amino triazole rings, which are found in some bio active molecules. However, additional studies are required in order to evaluate the scope and appUcability to more complex ynamides. 

Triazole as the keystone in glycosylated molecular architectures constructed by a click reaction 07CAJ700. 

Dondoni A (2007) Triazoles the keystone in glycosylated molecular architectures constmcted by a click reaction. Chem Asian J 2 700-708... 

Sen et al. used basic alumina as solid support for a novel one-pot synthesis of triazolyl Af-carboxamides 74 from glycosyl amines 72 without any solvent, ligand, or base (Scheme 6.19). Also, a number of biologically important unsymmetrical bis-1,2,3-triazoles were obtained by consecutive domino-click reaction [42]. 

An attractive library of nonhydrolyzable 1,2,3-triazole derivatives of sialic acid was developed using CuAAC reaction of glycosyl azide 83 with different terminal alkynes, and the developed series was examined for neuraminidase inhibitory activity. Compound 84, obtained by clicking of azide 83 with dec-l-yne, was recognized as potential lead compound (ICjg = 28 pM) than standard Neu5Ac2en. Similarly, other multivalent derivative 85 (ICjg = 17 pM) and dendrimer 86... 

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