Stereospecific synthesis of a GS 4104 metabolite: determination of absolute stereochemistry and influenza neuraminidase inhibitory activity

Bioorg Med Chem Lett. 1999 Oct 4;9(19):2811-4. doi: 10.1016/s0960-894x(99)00479-5.

Abstract

The total synthesis for the determination of the absolute stereochemistry of a GS 4104 metabolite 3 is described. In addition, the influenza neuraminidase inhibitory activity of 3 and related intermediates are reported.

MeSH terms

  • Acetamides / chemistry
  • Acetamides / pharmacology
  • Amines / chemical synthesis*
  • Amines / pharmacology
  • Antiviral Agents / chemical synthesis*
  • Enzyme Inhibitors / chemical synthesis
  • Enzyme Inhibitors / pharmacology
  • Esters / chemical synthesis
  • Molecular Conformation
  • Molecular Structure
  • Neuraminidase / antagonists & inhibitors*
  • Orthomyxoviridae / enzymology*
  • Oseltamivir
  • Prodrugs / chemistry
  • Prodrugs / metabolism

Substances

  • Acetamides
  • Amines
  • Antiviral Agents
  • Enzyme Inhibitors
  • Esters
  • Prodrugs
  • Oseltamivir
  • Neuraminidase