Syntheses of 2-deoxy-2,3-didehydro-N-acetylneuraminic acid analogues modified by α-acylaminoamido groups at the C-4 position using isocyanide-based four-component coupling and biological evaluation as inhibitors of human parainfluenza virus type 1

Chem Pharm Bull (Tokyo). 2013;61(1):69-74. doi: 10.1248/cpb.c12-00834.

Abstract

Novel sialidase inhibitors 11 having an α-acylaminoamido group at the C-4 position of Neu5Ac2en 1 against human parainfluenza virus type 1 (hPIV-1) were synthesized using one-pot isocyanide-based four-component condensation, and their inhibitory activities against hPIV-1 sialidase were studied. Compound 11b showed inhibitory activity (IC(50)=5.1 mM) against hPIV-1 sialidase. The degree of inhibition of 11b was much weaker than that of 1 (IC(50)=0.3 mM).

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Antiviral Agents / chemical synthesis
  • Antiviral Agents / chemistry*
  • Antiviral Agents / pharmacology*
  • Humans
  • 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 / virology
  • Structure-Activity Relationship

Substances

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