Stereospecific synthesis of a GS 4104 metabolite: determination of absolute stereochemistry and influenza neuraminidase inhibitory activity.
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.
Lew
W
W
Gilead Sciences Inc., Foster City, CA 94404, USA.
Escarpe
P A
PA
Mendel
D B
DB
Sweeny
D J
DJ
Kim
C U
CU
D000081:Acetamides / Q000737:chemistry / Q000494:pharmacology; D000588:Amines / Q000138:chemical synthesis* / Q000494:pharmacology; D000998:Antiviral Agents / Q000138:chemical synthesis*; D004791:Enzyme Inhibitors / Q000138:chemical synthesis / Q000494:pharmacology; D004952:Esters / Q000138:chemical synthesis; D008968:Molecular Conformation; D015394:Molecular Structure; D009439:Neuraminidase / Q000037:antagonists & inhibitors*; D009975:Orthomyxoviridae / Q000201:enzymology*; D053139:Oseltamivir; D011355:Prodrugs / Q000737:chemistry / Q000378:metabolism
D000081:Acetamides; D000588:Amines; D000998:Antiviral Agents; D004791:Enzyme Inhibitors; D004952:Esters; D011355:Prodrugs; D053139:Oseltamivir; D009439:Neuraminidase