2-Deoxy-2,3-didehydro-N-acetylneuraminic acid analogues structurally modified at the C-4 position: synthesis and biological evaluation as inhibitors of human parainfluenza virus type 1

Bioorg Med Chem. 2006 Dec 1;14(23):7893-7. doi: 10.1016/j.bmc.2006.07.045.

Abstract

To explore the influence of binding to human parainfluenza virus type 1 (hPIV-1), a series of 4-O-substituted Neu5Ac2en derivatives 6a-e was synthesized and tested for their ability to inhibit hPIV-1 sialidase. Among compounds 6a-e, the 4-O-ethyl-Neu5Ac2en derivative 6b showed the most potent inhibitory activity (IC50 6.3 microM) against hPIV-1 sialidase.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Antiviral Agents / chemical synthesis*
  • Antiviral Agents / pharmacology
  • Enzyme Inhibitors / chemical synthesis
  • Enzyme Inhibitors / pharmacology
  • Humans
  • Inhibitory Concentration 50
  • N-Acetylneuraminic Acid / analogs & derivatives*
  • N-Acetylneuraminic Acid / chemical synthesis
  • N-Acetylneuraminic Acid / chemistry
  • N-Acetylneuraminic Acid / pharmacology
  • Neuraminidase / antagonists & inhibitors*
  • Parainfluenza Virus 1, Human / drug effects
  • Parainfluenza Virus 1, Human / enzymology*
  • Respirovirus Infections / drug therapy
  • Respirovirus Infections / enzymology
  • Structure-Activity Relationship

Substances

  • Antiviral Agents
  • Enzyme Inhibitors
  • 2-deoxy-2,3-dehydro-N-acetylneuraminic acid
  • Neuraminidase
  • N-Acetylneuraminic Acid