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

Paul Brémond; Gérard Audran; Honoré Monti; Erik De Clercq; Christophe Pannecouque

doi:10.1055/s-0028-1083213

PAPER

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

Paul Brémond^a, Gérard Audran*^a, Honoré Monti^a, Erik De Clercq^b, Christophe Pannecouque^b
^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

Abstract

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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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