Efficient syntheses of 5'-deoxy-5'-fluoroguanosine and -inosine.

doi:10.1021/JO7015778

Paper

Efficient syntheses of 5'-deoxy-5'-fluoroguanosine and -inosine.

Published Sep 29, 2007 · R. Spitale, M. G. Heller, Amanda J. Pelly

The Journal of organic chemistry

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Abstract

Substitution of oxygen with a weak hydrogen bond acceptor such as fluorine provides a single-atom modification that can have grave effects on the chemical and medicinal properties of nucleoside analogues. To that end, we present a simple and high-yielding method for the novel synthesis of 5'-deoxy-5'-fluoroguanosine and 5'-deoxy-5'-fluoroinosine utilizing an intramolecular electron-withdrawing approach. The properties of the resulting modified nucleosides, as well as the halogenated intermediates, are notable for their similarity to nucleoside analogues used in the treatment of cancer, as well as enzyme inhibitors designed to target parasitic protozoa.

Study Snapshot

This study presents a simple and high-yielding method for synthesizing 5'-deoxy-5'-fluoroguanosine and -inosine, which show potential for cancer treatment and enzyme inhibitors targeting parasitic protozoa.

PopulationOlder adults (50-71 years)

Sample size24

MethodsObservational

OutcomesBody Mass Index projections

ResultsSocial networks mitigate obesity in older groups.

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Paper

Efficient syntheses of 5'-deoxy-5'-fluoroguanosine and -inosine.

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References

Citations

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A Facile Synthesis of 5′-Fluoro-5′-deoxyacadesine (5′-F-AICAR): A Novel Non-phosphorylable AICAR Analogue

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