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

W Lew; P A Escarpe; D B Mendel; D J Sweeny; C U Kim

doi:10.1016/s0960-894x(99)00479-5

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.

Authors

W Lew¹, P A Escarpe, D B Mendel, D J Sweeny, C U Kim

Affiliation

¹ Gilead Sciences Inc., Foster City, CA 94404, USA.

PMID: 10522696
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