Synthesis and antiviral activity of 1,2,3-triazolyl nucleoside analogues with -acetyl-d-glucosamine residue.

A series of 1,2,3-triazolyl nucleoside analogues bearing -acetyl-D-glucosamine residue was synthesized by the copper-catalyzed alkyne-azide cycloaddition (CuAAC) reaction of 1-ω-alkynyl derivatives of uracil, 6-methyluracil, thymine and 3,4,6-tri--acetyl-2-deoxy-2-acetamido-β-D-glucopyranosyl azide. Antiviral assays revealed the lead compound which showed both the same activity against the influenza virus A H1N1 (IC=70.7 µM) as the antiviral drug Rimantadine in control (IC=77 µM) and good activity against Coxsackievirus B3 (IC=13.9 µM) which was one and a half times higher than the activity of the antiviral drug Pleconaril in control (IC=21.6 µM). According to molecular docking simulations, the antiviral activity of the lead compound against Coxsackie B3 virus can be explained by its binding to a key fragment of the capsid surface of this virus.