Abstract
8-Arylinosines have been scarcely studied for therapeutic purposes, probably due to difficulties in their synthesis. The recently described direct arylation reaction at position 8 of purine nucleosides has been employed to synthesize a series of 8-aryl and 8-pyridylinosines. These compounds have been studied for hydrolytic stability and subjected to biological evaluation. Three compounds have shown a pronounced specific inhibition of Plasmodium falciparum-encoded purine nucleoside phosphorylase, an important target for antimalarial chemotherapy.
Keywords:
Antiviral; Direct C-arylation; Inosine; Microwave-assisted synthesis; Phosphorylase.
Copyright © 2014 Elsevier Masson SAS. All rights reserved.
Publication types
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Research Support, Non-U.S. Gov't
MeSH terms
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Animals
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Anti-Bacterial Agents / chemical synthesis
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Anti-Bacterial Agents / chemistry
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Anti-Bacterial Agents / pharmacology*
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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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Chlorocebus aethiops
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DNA Viruses / drug effects
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Dogs
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Dose-Response Relationship, Drug
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Drug Screening Assays, Antitumor
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Enzyme Inhibitors / chemical synthesis
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Enzyme Inhibitors / chemistry
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Enzyme Inhibitors / pharmacology*
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Escherichia coli / drug effects
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HeLa Cells
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Humans
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Inosine / analogs & derivatives
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Inosine / chemical synthesis
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Inosine / pharmacology*
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Madin Darby Canine Kidney Cells
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Microbial Sensitivity Tests
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Microwaves
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Molecular Conformation
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Mycoplasma hyorhinis / drug effects
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Plasmodium falciparum / enzymology*
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Purine-Nucleoside Phosphorylase / antagonists & inhibitors*
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Purine-Nucleoside Phosphorylase / metabolism
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RNA Viruses / drug effects
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Vero Cells
Substances
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Anti-Bacterial Agents
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Antiviral Agents
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Enzyme Inhibitors
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Inosine
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Purine-Nucleoside Phosphorylase