2beta,3beta-Difluorosialic acid derivatives structurally modified at the C-4 position: synthesis and biological evaluation as inhibitors of human parainfluenza virus type 1

Carbohydr Res. 2004 May 17;339(7):1367-72. doi: 10.1016/j.carres.2004.02.029.

Abstract

A series of 4-O-substituted 2beta,3beta-difluorosialic acid derivatives (3a-d) has been synthesized. A key intermediate was synthesized efficiently by the electrophilic syn-addition of fluorine to the double bond of a glycal precursor using molecular fluorine or xenon difluoride in the presence of BF(3).OEt(2). Among compounds 3a-d, the 4-O-thiocarbamoylmethyl derivative 3c showed the most potent inhibitory activity against sialidase of human parainfluenza virus type 1. [structure: see text].

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Antiviral Agents / chemical synthesis*
  • Antiviral Agents / chemistry
  • Antiviral Agents / pharmacology*
  • Molecular Structure
  • Neuraminidase / antagonists & inhibitors*
  • Parainfluenza Virus 1, Human / drug effects
  • Parainfluenza Virus 1, Human / enzymology*
  • Sialic Acids / chemical synthesis*
  • Sialic Acids / chemistry
  • Sialic Acids / pharmacology*

Substances

  • Antiviral Agents
  • Sialic Acids
  • Neuraminidase