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

  • Bioorg Med Chem. 2007 Jan 15;15(2):839-46. doi: 10.1016/j.bmc.2006.10.043.
Jagadeeshwar R Rao  1 ,  Raymond F Schinazi ,  Chung K Chu
Affiliations
  • 1. The University of Georgia College of Pharmacy, Athens, GA 30602, USA.
PMID: 17085053 DOI: 10.1016/j.bmc.2006.10.043
Abstract

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.