Synthesis, antiviral activity, and stability of nucleoside analogs containing tricyclic bases.
A series of 3,9-dihydro-9-oxo-5H-imidazo[1,2-A]purine nucleosides (tricylic nucleosides) were synthesized from 9-[4-alpha-(hydroxymethyl)cyclopent-2-ene-1-alpha-yl]guanine (CBV) 5, (-)-beta-D-(2R,4R)-1,3-dioxolane-guanosine (DXG) 6, 3'-azido-3'-deoxy-guanosine (AZG) 7, and 2'-C-methylguanosine 8. Their in vitro activity against HIV and HCV was evaluated and correlated to their ability to degrade to their purine counterpart.
Department of Pediatrics, Center for AIDS Research, Veterans Affairs Medical Center, Laboratory of Biochemical Pharmacology, Emory University School of Medicine, Atlanta, GA 30033, USA.
Franck
F
Amblard
Emilie
E
Fromentin
Mervi
M
Detorio
Alexander
A
Obikhod
Kimberly L
KL
Rapp
Tamara R
TR
McBrayer
Tony
T
Whitaker
Steven J
SJ
Coats
Raymond F
RF
Schinazi
D000818:Animals; D000998:Antiviral Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology* / Q000633:toxicity; D002470:Cell Survival / Q000187:drug effects; D002478:Cells, Cultured; D002522:Chlorocebus aethiops; D006678:HIV / Q000187:drug effects*; D016174:Hepacivirus / Q000187:drug effects*; D018259:Herpesvirus 1, Human / Q000187:drug effects; D006801:Humans; D009705:Nucleosides / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology* / Q000633:toxicity; D014709:Vero Cells
D000998:Antiviral Agents; D009705:Nucleosides