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.
Publication types
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Research Support, U.S. Gov't, P.H.S.
MeSH terms
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Adenosine / analogs & derivatives*
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Adenosine / chemical synthesis
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Adenosine / pharmacology
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Animals
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Antiviral Agents / chemical synthesis*
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Antiviral Agents / pharmacology
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Cell Line
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Cell Survival / drug effects
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Cowpox virus / drug effects
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Cytidine / analogs & derivatives*
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Cytidine / chemical synthesis
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Cytidine / pharmacology
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Monkeypox virus / drug effects
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Nucleosides / chemical synthesis*
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Nucleosides / pharmacology
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Orthopoxvirus / drug effects*
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Structure-Activity Relationship
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Variola virus / drug effects
Substances
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Antiviral Agents
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Nucleosides
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Cytidine
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cyclopentenyl cytosine
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neplanocin A
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Adenosine