Antiviral activity of cyclopentenyl nucleosides against orthopox viruses (Smallpox, monkeypox and cowpox)

  • Bioorg Med Chem Lett. 2003 Jan 6;13(1):9-12. doi: 10.1016/s0960-894x(02)00841-7.
C K Chu  1 ,  Y H Jin ,  R O Baker ,  J Huggins
Affiliations
  • 1. Department of Pharmaceutical and Biomedical Science, College of Pharmacy, The University of Georgia, Athens 30602, USA. [email protected]
PMID: 12467606 DOI: 10.1016/s0960-894x(02)00841-7
Abstract

An improved method for the synthesis of enantiomerically pure D-cyclopentenyl nucleosides has been accomplished and their Antiviral activity against orthopox viruses have been evaluated. The key intermediate, L-cyclopent-2-enone 13 was prepared from D-ribose using a ring closing metathesis reaction in eight steps. Among the synthesized nucleosides, the adenine 2 (Neplanocin A), cytosine 14, and 5-F-cytosine 15 analogues exhibited potent anti-orthopox virus activity, including smallpox virus.