Syntheses of triazole-modified zanamivir analogues via click chemistry and anti-AIV activities

Bioorg Med Chem Lett. 2006 Oct 1;16(19):5009-13. doi: 10.1016/j.bmcl.2006.07.047. Epub 2006 Jul 28.

Abstract

Sixteen novel 4-triazole-modified zanamivir (1) analogues were synthesized using the click reactions, and their inhibitory activities against avian influenza virus (AIV, H5N1) were determined. Compound 3b exerts promising inhibitory activity with EC(50) of 6.4 microM, which is very close to that of zanamivir (EC(50) = 2.8 microM). Molecular modeling provided the information about the binding model between inhibitors and neuraminidase, which are in good agreement with inhibitory activities.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Antiviral Agents / chemical synthesis*
  • Antiviral Agents / pharmacology
  • Enzyme Inhibitors / chemistry
  • Enzyme Inhibitors / metabolism
  • Guanidines / chemical synthesis
  • Guanidines / chemistry*
  • Guanidines / pharmacology
  • Humans
  • Influenza A Virus, H5N1 Subtype / drug effects*
  • Influenza, Human / prevention & control
  • Models, Molecular
  • Neuraminidase / antagonists & inhibitors
  • Neuraminidase / metabolism
  • Pyrans / chemical synthesis
  • Pyrans / chemistry*
  • Pyrans / pharmacology
  • Sialic Acids / chemical synthesis
  • Sialic Acids / chemistry*
  • Sialic Acids / pharmacology
  • Structure-Activity Relationship
  • Triazoles
  • Zanamivir

Substances

  • Antiviral Agents
  • Enzyme Inhibitors
  • Guanidines
  • Pyrans
  • Sialic Acids
  • Triazoles
  • Neuraminidase
  • Zanamivir