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Synthesis of 5-haloethynyl- and 5-(1,2-dihalo)vinyluracil nucleosides: antiviral activity and cellular toxicity. 2005
Vanessa Escuret, and
Vincent Aucagne, and
Nicolas Joubert, and
David Durantel, and
Kimberly L Rapp, and
Raymond F Schinazi, and
Fabien Zoulim, and
Luigi A Agrofoglio
Institut de Chimie Organique et Analytique, ICOA UMR 6005, UFR Sciences, BP 6759, 45067 Orléans Cedex 2, France.
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).
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