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Synthesis 2009(2): 290-296  
DOI: 10.1055/s-0028-1083213
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Synthesis and Antiviral Evaluation of (-)-3′-Methylcarbovir, (-)-3′-Methylabacavir, and Modified Purine Analogues

Paul Brémonda, Gérard Audran*a, Honoré Montia, Erik De Clercqb, Christophe Pannecouqueb
a Institut des Sciences Moléculaires de Marseille, ISM2 - UMR CNRS 6263, Equipe StéRéO, Université Paul Cézanne, 13397 Marseille Cedex 20, France
Fax: +33(491)288862; e-Mail: g.audran@univ-cezanne.fr;
b Rega Institute for Medical Research, Katholieke Universiteit Leuven, 10 Minderbroedersstraat, 3000 Leuven, Belgium
Further Information

Publication History

Received 17 July 2008
Publication Date:
30 October 2008 (online)

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Abstract

Starting from ethyl (1S,4R)-4-hydroxy-2-methylcyclopent-2-ene-1-carboxylate, as a common enantiopure building block readily obtained by enzymatic kinetic resolution of the corresponding racemic derivative, 3′-methylcarbovir, 3′-methylabacavir, and three modified analogues were synthesized via the linear construction of the purine heterocycles. These derivatives were evaluated as potential agents against HIV-1, HIV-2, and other important viral pathogens. None of the new compounds had significant antiviral activity at a concentration of 100 µg˙mL-¹, which was the highest concentration tested.

Key words

stereoselective synthesis - azides - carbocyclic nucleosides - nucleobases - antiviral agents

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