Nucleosides and Nucleotides p. 1397 - 1409 (1996)
Update date:2022-08-15
Topics:
Mourier, Nicolas
Trabaud, Carole
Niddam, Valerie
Graciet, Jean-Christophe
Camplo, Michel
Chermann, Jean-Claude
Kraus, Jean-Louis
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.
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