Synthesis and anti-influenza evaluation of polyvalent sialidase inhibitors bearing 4-guanidino-Neu5Ac2en derivatives

Bioorg Med Chem Lett. 2002 Aug 5;12(15):1929-32. doi: 10.1016/s0960-894x(02)00330-x.

Abstract

We synthesized polyvalent sialidase inhibitors bearing 4-guanidino-Neu5Ac2en analogues on the polyglutamic acid back bone, via a spacer of alkyl ether at the C-7 position. These multivalent conjugates 9 and 10 showed enhancement of antiviral activity against infuenza A virus and more potent efficacy in vivo relative to a monomeric sialidase inhibitor.

MeSH terms

  • Animals
  • Antiviral Agents / chemistry*
  • Antiviral Agents / pharmacology*
  • Enzyme Inhibitors / chemical synthesis*
  • Enzyme Inhibitors / pharmacology*
  • Glutamic Acid / chemistry
  • Glyceryl Ethers / chemistry
  • Guanidine / analogs & derivatives*
  • Guanidine / chemical synthesis
  • Guanidine / pharmacology
  • Guanidines
  • Influenza A virus / drug effects
  • Influenza A virus / enzymology
  • Inhibitory Concentration 50
  • Mice
  • N-Acetylneuraminic Acid / analogs & derivatives*
  • N-Acetylneuraminic Acid / chemistry*
  • N-Acetylneuraminic Acid / pharmacology*
  • Neuraminidase / antagonists & inhibitors*
  • Neuraminidase / chemistry
  • Orthomyxoviridae Infections / drug therapy
  • Pyrans
  • Sialic Acids
  • Structure-Activity Relationship
  • Viral Plaque Assay
  • Zanamivir

Substances

  • Antiviral Agents
  • Enzyme Inhibitors
  • Glyceryl Ethers
  • Guanidines
  • Pyrans
  • Sialic Acids
  • 2-deoxy-2,3-dehydro-N-acetylneuraminic acid
  • Glutamic Acid
  • Neuraminidase
  • N-Acetylneuraminic Acid
  • Guanidine
  • Zanamivir