Synthesis and anti-HIV evaluation of new 5-substituted-2',3'-dideoxy- 3'-thiauridine nucleosides

Article abstract of DOI:10.1080/07328319608002439

On the basis of molecular modeling calculations using GenMol software, new 5-substituted-2',3'-dideoxy-3'-thiauridine were designed as possible anti-HIV reverse transcriptase inhibitors. The synthesis of the key intermediate 5-carboxy-2',3'-dideoxy-3'-thiauridine was achieved through the condensation of the fully silylated 5-carboxyuracil on 2-benzoyl methyl-5- acetoxy-1,3-oxathiolane using trimethylsilyl triflate (TMSOTf). This latter compound was condensed with 2-(N-tert-Butoxycarbonyl)-1-aminoethane in the presence of N,N-diisopropylethylamine (DIEA). The subsequent carboxamide deprotection led to the final compounds. These new analogues were evaluated for their anti-HIV-1 activities on infected MT₄ cells but no significant protection was observed. Electronic and structural parameters considered in this model were not sufficient to predict any active anti-HIV molecular structures.

Full text of DOI:10.1080/07328319608002439

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Nucleosides and Nucleotides
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Synthesis and Anti-HIV Evaluation of
New 5-Substituted-2′,3′-Dideoxy-3′-
thiauridine Nucleosides
a b
a b
a b
Nicolas Mourier
, Carole Trabaud
, Valerie Niddam
, Jean-
a b
a b
b
Christophe Graciet
, Michel Camplo
, Jean-Claude Chermann
a b
&
a
Jean-Louis Kraus
Laboratoire de Chimie Biomoléculaire , Faculté des Sciences de
Luminy , case 901, 13288, MARSEILLE, CEDEX 9, FRANCE
b
INSERM Unité U-322 , Unité des Rétrovirus et Maladies associées,
Campus Universitaire de Luminy , BP 33, 13273, MARSEILLE, CEDEX
9, FRANCE Fax:
Published online: 22 Aug 2006.
To cite this article: Nicolas Mourier , Carole Trabaud , Valerie Niddam , Jean-Christophe Graciet ,
Michel Camplo , Jean-Claude Chermann & Jean-Louis Kraus (1996) Synthesis and Anti-HIV Evaluation
of New 5-Substituted-2′,3′-Dideoxy-3′-thiauridine Nucleosides, Nucleosides and Nucleotides, 15:7-8,
1397-1409, DOI: 10.1080/07328319608002439
To link to this article: http://dx.doi.org/10.1080/07328319608002439
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