Enantioselective synthesis and antiviral activity of purine and pyrimidine cyclopentenyl C-nucleosides

• Published in: Bioorganic & medicinal chemistry Vol. 15; no. 2; pp. 839 - 846
• Main Authors: Rao, Jagadeeshwar R., Schinazi, Raymond F., Chu, Chung K.
• Format: Journal Article
• Language: English
• Published: England Elsevier Ltd 15.01.2007
• Subjects: Animals; Anti-HIV Agents - chemical synthesis; Anti-HIV Agents - pharmacology; Antiviral activity; Antiviral Agents - chemical synthesis; Antiviral Agents - pharmacology; Carbocyclic C-nucleosides; Chlorocebus aethiops; Cyclopentanes - chemical synthesis; Cyclopentanes - pharmacology; Drug Screening Assays, Antitumor; Enantioselective synthesis; HIV-1 - drug effects; Human immunodeficiency virus; Humans; Indicators and Reagents; Magnetic Resonance Spectroscopy; Nucleosides - chemical synthesis; Nucleosides - pharmacology; Spectrophotometry, Ultraviolet; Stereoisomerism; Vero Cells; Viruses - drug effects; Enantioselective synthesis; Carbocyclic C-nucleosides; Antiviral activity
• ISSN: 0968-0896; 1464-3391
• DOI: 10.1016/j.bmc.2006.10.043

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.