Antiviral activity of cyclopentenyl nucleosides against orthopox viruses (Smallpox, monkeypox and cowpox).
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.
Chu
C K
CK
Department of Pharmaceutical and Biomedical Science, College of Pharmacy, The University of Georgia, Athens 30602, USA. dchu@rx.uga.edu
Jin
Y H
YH
Baker
R O
RO
Huggins
J
J
D000241:Adenosine / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000494:pharmacology; D000818:Animals; D000998:Antiviral Agents / Q000138:chemical synthesis* / Q000494:pharmacology; D002460:Cell Line; D002470:Cell Survival / Q000187:drug effects; D015608:Cowpox virus / Q000187:drug effects; D003562:Cytidine / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000494:pharmacology; D008993:Monkeypox virus / Q000187:drug effects; D009705:Nucleosides / Q000138:chemical synthesis* / Q000494:pharmacology; D018155:Orthopoxvirus / Q000187:drug effects*; D013329:Structure-Activity Relationship; D012901:Variola virus / Q000187:drug effects
D000998:Antiviral Agents; D009705:Nucleosides; D003562:Cytidine; C045911:cyclopentenyl cytosine; C031096:neplanocin A; D000241:Adenosine