First example of phosphoramidate approach applied to a 4'-substituted purine nucleoside (4'-azidoadenosine): conversion of an inactive nucleoside to a submicromolar compound versus hepatitis C virus.

@article{Perrone2007FirstEO,
  title={First example of phosphoramidate approach applied to a 4'-substituted purine nucleoside (4'-azidoadenosine): conversion of an inactive nucleoside to a submicromolar compound versus hepatitis C virus.},
  author={Plinio Perrone and Felice Daverio and Rocco Valente and Sonal Rajyaguru and Joseph A. Martin and Vincent J.-P. Lévêque and Sophie Le Pogam and Isabel Nájera and Klaus Klumpp and David Bernard Smith and Christopher Mcguigan},
  journal={Journal of medicinal chemistry},
  year={2007},
  volume={50 22},
  pages={
          5463-70
        }
}
We report on the synthesis of the anti hepatitis C virus (HCV) agent 4'-azidoadenosine (1) and the application of the phosphoramidate ProTide technology to this nucleoside. The synthesis of 1 was achieved through an epoxide intermediate followed by regio- and stereoselective ring opening by azidotrimethylsilane in the presence of a Lewis acid. Compound 1 did not inhibit HCV replication in cell culture at concentrations up to 0.1 mM. However, a submicromolar active agent could be derived from 1… 
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