Enantioselective synthesis and antiviral activity of purine and pyrimidine cyclopentenyl C-nucleosides.
The enantiomerically pure carbocyclic purine and pyrimidine C-nucleosides 1-4 were synthesized via the key intermediate, 2,3-(isopropylidenedioxy)-4-(trityloxymethyl)-4-cyclopenten-1-ol (5), which was prepared from d-ribose in eight steps. Synthesized compounds were evaluated as potential antiviral agents against HIV, SARSCoV, Punta Toro, West Nile, and Cowpox viruses. However, only 9-deazaneplanocin A (1) exhibited moderate anti-HIV activity.
Rao
Jagadeeshwar R
JR
The University of Georgia College of Pharmacy, Athens, GA 30602, USA.
Schinazi
Raymond F
RF
Chu
Chung K
CK
D000818:Animals; D019380:Anti-HIV Agents / Q000138:chemical synthesis / Q000494:pharmacology; D000998:Antiviral Agents / Q000138:chemical synthesis* / Q000494:pharmacology*; D002522:Chlorocebus aethiops; D003517:Cyclopentanes / Q000138:chemical synthesis* / Q000494:pharmacology*; D004354:Drug Screening Assays, Antitumor; D015497:HIV-1 / Q000187:drug effects; D006801:Humans; D007202:Indicators and Reagents; D009682:Magnetic Resonance Spectroscopy; D009705:Nucleosides / Q000138:chemical synthesis* / Q000494:pharmacology*; D013056:Spectrophotometry, Ultraviolet; D013237:Stereoisomerism; D014709:Vero Cells; D014780:Viruses / Q000187:drug effects
D019380:Anti-HIV Agents; D000998:Antiviral Agents; D003517:Cyclopentanes; D007202:Indicators and Reagents; D009705:Nucleosides