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Article Dans Une Revue European Journal of Organic Chemistry Année : 2011

Synthesis and Biological Evaluation of 4′-C,3′-O-Propylene-Linked Bicyclic Nucleosides

Robert Zalesny
  • Fonction : Auteur
Hans Agren
  • Fonction : Auteur
Sylvio Canuto
Tami Mcbrayer
  • Fonction : Auteur
Mervi Detorio
  • Fonction : Auteur
Jong-Hyun Cho
  • Fonction : Auteur

Résumé

A set of pyrimidine nucleosides fused with a 4'-C,3'-O-propylene bridge was successfully synthesised in 12 steps from 1,2:5,6-di-O-isopropylidene-alpha-D-glucofuranose, an inexpensive starting material, based on a ring-closing metathesis (RCM) reaction followed by Vorbruggen-type nucleobase coupling. Antiviral and cytotoxicity activities of the targeted modified nucleosides, as well as their phosphoramidate prodrugs, are described.

Dates et versions

hal-02142274 , version 1 (28-05-2019)

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Citer

Marcelo G. Vivas, Daniel L. Silva, Jeremy Malinge, Mohammed Boujtita, Robert Zalesny, et al.. Synthesis and Biological Evaluation of 4′-C,3′-O-Propylene-Linked Bicyclic Nucleosides. European Journal of Organic Chemistry, 2011, 36, pp.7390-7399. ⟨10.1002/ejoc.201100859⟩. ⟨hal-02142274⟩
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