Synthesis of a new family of acyclic nucleoside phosphonates, analogues of TPases transition states

A 6-step procedure was developed for the synthesis of a new family of acyclic nucleoside phosphonates (ANPs), "PHEEPA" [(2-pyrimidinyl-2-(2-hydroxyethoxy)ethyl)phosphonic acids] in overall yields ranging from 4.5% to 32%. These compounds, which possess on one side a hydroxy function and on...

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Bibliographic Details
Published in:Organic & biomolecular chemistry 2012-05, Vol.10 (17), p.3448-3454
Main Authors: Dayde, Bénédicte, Benzaria, Samira, Pierra, Claire, Gosselin, Gilles, Surleraux, Dominique, Volle, Jean-Noël, Pirat, Jean-Luc, Virieux, David
Format: Article
Language:English
Subjects:
Biomimetic Materials - chemical synthesis
Biomimetic Materials - chemistry
Chemical Sciences
Chemistry Techniques, Synthetic - methods
Nucleosides - chemistry
Organic chemistry
Organophosphonates - chemical synthesis
Organophosphonates - chemistry
Pyrimidines - chemical synthesis
Pyrimidines - chemistry
Thymidine Phosphorylase - chemistry
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Summary:A 6-step procedure was developed for the synthesis of a new family of acyclic nucleoside phosphonates (ANPs), "PHEEPA" [(2-pyrimidinyl-2-(2-hydroxyethoxy)ethyl)phosphonic acids] in overall yields ranging from 4.5% to 32%. These compounds, which possess on one side a hydroxy function and on the other side a phosphonate group, can be considered either as potential antiviral agents or as transition state analogues of nucleoside phosphorylases such as thymidine phosphorylase.
ISSN:1477-0520
1477-0539
DOI:10.1039/c2ob25131k