Synthesis and biological evaluation of lipophilic teicoplanin pseudoaglycon derivatives containing a substituted triazole function

A series of lipophilic teicoplanin pseudoaglycon derivatives, including alkyl-, aryl-, calixarene- and protected sugar-containing conjugates, were prepared using azide–alkyne click chemistry. Out of the conditions applied, the CuSO 4 –ascorbate reagent system proved to be more efficient than the Cu(I)I–Et 3 N-mediated reaction. Some of the new compounds have high in vitro activity against glycopeptide-resistant Gram-positive bacteria, including vanA-positive Enterococcus faecalis . A few of them also display promising in vitro anti-influenza activity.