Synthesis of 5-haloethynyl- and 5-(1,2-dihalo)vinyluracil nucleosides: Antiviral activity and cellular toxicity - CNRS - Centre national de la recherche scientifique Accéder directement au contenu
Article Dans Une Revue Bioorganic and Medicinal Chemistry Année : 2005

Synthesis of 5-haloethynyl- and 5-(1,2-dihalo)vinyluracil nucleosides: Antiviral activity and cellular toxicity

David Durantel
Kimberly Rapp
  • Fonction : Auteur
Raymond Schinazi
  • Fonction : Auteur
Fabien Zoulim

Résumé

In this article, we report the synthesis of hitherto unknown 5-haloethynyl and 5-(1,2-dihalo)vinyluracil nucleosides in the 2'-deoxy, 3'-deoxy- and ribosyl series, and we discuss their in vitro anti-HIV and anti-HCV activities and cellular toxicitites. As a result, on the basis of their selectivity index (SI) obtained with the HCV replicon system, but also on their cytotoxicity on peripheral blood mononuclear, CEM and VERO cell lines, the best compounds were the 5-bromoethynyluridine (SI = 3.2) and the 5-(1-chloro-2-iodo)vinyluridine (SI > 2.8).

Dates et versions

hal-02086013 , version 1 (01-04-2019)

Identifiants

Citer

Vanessa Escuret, Vincent Aucagne, Nicolas Joubert, David Durantel, Kimberly Rapp, et al.. Synthesis of 5-haloethynyl- and 5-(1,2-dihalo)vinyluracil nucleosides: Antiviral activity and cellular toxicity. Bioorganic and Medicinal Chemistry, 2005, 13 (21), pp.6015-6024. ⟨10.1016/j.bmc.2005.06.021⟩. ⟨hal-02086013⟩
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