Abstract
An efficient and facile synthesis of a large series of diverse 6-(N-substituted aminomethyl)-, 6-(O-substituted hydroxymethyl)- and 6-(S-substituted sulfanylmethyl)purine nucleosides (55 examples of both ribo- and 2'-deoxyribonucleosides), aimed at identifying novel homologues of natural nucleosides, was developed. The key transformation involved nucleophilic substitutions of Tol-protected 6-(mesyloxymethyl)purine nucleosides by primary or secondary amines, alcoholates or thiolates. While the 2'-deoxyribonucleosides were inactive, the ribonucleosides exerted considerable cytostatic effects and some anti-HCV activity with low selectivity.
Publication types
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Research Support, Non-U.S. Gov't
MeSH terms
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Amination
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Animals
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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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Cell Line, Tumor
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Cytostatic Agents / chemical synthesis*
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Cytostatic Agents / chemistry
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Cytostatic Agents / pharmacology*
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Hepacivirus / drug effects*
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Humans
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Hydroxylation
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Mesylates / chemistry
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Methylation
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Mice
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Molecular Structure
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Purine Nucleosides / chemical synthesis*
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Purine Nucleosides / chemistry
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Purine Nucleosides / pharmacology*
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Structure-Activity Relationship
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Sulfur Compounds / chemical synthesis
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Sulfur Compounds / chemistry
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Sulfur Compounds / pharmacology
Substances
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Antiviral Agents
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Cytostatic Agents
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Mesylates
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Purine Nucleosides
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Sulfur Compounds