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.
Amblard
Franck
F
Department of Pediatrics, Center for AIDS Research, Veterans Affairs Medical Center, Laboratory of Biochemical Pharmacology, Emory University School of Medicine, Atlanta, GA 30033, USA.
Fromentin
Emilie
E
Detorio
Mervi
M
Obikhod
Alexander
A
Rapp
Kimberly L
KL
McBrayer
Tamara R
TR
Whitaker
Tony
T
Coats
Steven J
SJ
Schinazi
Raymond F
RF
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