Abstract
The Simmons-Smith-Furukawa reaction was used to generate 4'/5'-spirocyclopropanated uridine analogs from electron-rich exocyclic enol esters. During synthesis, the native hydroxylation pattern of the nucleoside is preserved and offers the possibility for a late stage 5'-phosphorylation at the spirocyclopropanol moiety. All synthesized spirocyclopropanated uridine derivatives, including the corresponding 5'-monophosphate (cpUMP), were evaluated with respect to their antiviral activity in an HRSV assay showing moderate, but promising activity.
Publication types
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Research Support, Non-U.S. Gov't
MeSH terms
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Antiviral Agents / chemical synthesis
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Antiviral Agents / chemistry
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Antiviral Agents / pharmacology*
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Crystallography, X-Ray
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Cyclopropanes / chemical synthesis
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Cyclopropanes / chemistry
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Cyclopropanes / pharmacology*
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Microbial Sensitivity Tests
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Models, Molecular
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Molecular Conformation
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Respiratory Syncytial Virus, Human / drug effects*
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Spiro Compounds / chemical synthesis
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Spiro Compounds / chemistry
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Spiro Compounds / pharmacology*
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Uridine / analogs & derivatives
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Uridine / chemical synthesis
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Uridine / pharmacology*
Substances
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Antiviral Agents
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Cyclopropanes
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Spiro Compounds
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cyclopropane
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Uridine