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Org Biomol Chem. 2008 Apr 21;6(8):1396-409. doi: 10.1039/b800598b. Epub 2008 Feb 28.

Synthesis of sialoclusters appended to calix[4]arene platforms via multiple azide-alkyne cycloaddition. New inhibitors of hemagglutination and cytopathic effect mediated by BK and influenza A viruses.

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Dipartimento di Chimica, Laboratorio di Chimica Organica, Università di Ferrara, Via Borsari 46, I-44100, Ferrara, Italy.


Tetra- and octavalent sialoside clusters were prepared in good yields exploiting for the first time the multiple copper-catalyzed cycloaddition of a propargyl thiosialoside with calix[4]arene polyazides. The cycloadducts featured the hydrolytically stable carbon-sulfur bond at the anomeric position and the 1,4-disubstituted triazole ring as the spacer between the sialic acid moieties and the platform. It was demonstrated that these unnatural motifs did not hamper the desired biological activity of the sialoclusters. In fact, they were able to inhibit, at submillimolar concentrations, the hemagglutination and the viral infectivity mediated both by BK and influenza A viruses.

[Indexed for MEDLINE]

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