Synthesis and anti-HIV activity of 2'-fluorine modified nucleoside phosphonates: analogs of GS-9148.
Modified purine analogs of GS-9148 [5-(6-amino-purin-9-yl)-4-fluoro-2,5-dihydro-furan-2-yloxymethyl]-phosphonic acid (2'-Fd4AP) were synthesized and their anti-HIV potency evaluated. The antiviral activity of guanosine analog (2'-Fd4GP) was comparable that of to 2'-Fd4AP in MT-2 cells, but selectivity was reduced.
Mackman
Richard L
RL
Gilead Sciences, Inc., 333 Lakeside Drive, Foster City, CA 94404, USA. rmackman@gilead.com
Lin
Kuei-Ying
KY
Boojamra
Constantine G
CG
Hui
Hon
H
Douglas
Janet
J
Grant
Deborah
D
Petrakovsky
Oleg
O
Prasad
Vidya
V
Ray
Adrian S
AS
Cihlar
Tomas
T
D019380:Anti-HIV Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D005461:Fluorine / Q000737:chemistry*; D006151:Guanosine / Q000031:analogs & derivatives* / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D006801:Humans; D015394:Molecular Structure; D009705:Nucleosides / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D063065:Organophosphonates / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D018894:Reverse Transcriptase Inhibitors / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D013329:Structure-Activity Relationship; D015215:Zidovudine / Q000494:pharmacology
D019380:Anti-HIV Agents; D009705:Nucleosides; D063065:Organophosphonates; D018894:Reverse Transcriptase Inhibitors; D006151:Guanosine; D005461:Fluorine; D015215:Zidovudine; C527398:GS-9148