Synthesis 2008(20): 3253-3260  
DOI: 10.1055/s-0028-1083146
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Stereoselective Synthesis of Novel Aristeromycin Analogues as Potential Antiviral Agents

Paul Brémonda, Gérard Audran*a, Honoré Montia, Erik De Clercqb
a Institut des Sciences Moléculaires de Marseille, ISM2 - UMR CNRS 6263, Equipe STéRéO, Université Paul Cézanne, Aix-Marseille III, 13397 Marseille Cedex 20, France
Fax: +33(4)91288862; 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 3 June 2008
Publication Date:
25 September 2008 (online)

Abstract

A series of 3′-methyl-branched and purine-modified analogues of aristeromycin were synthesized via the SN2 displacement of a key triflate, which was prepared from a readily available enantiopure building block in eight steps. The synthesized compounds were evaluated as potential antiviral agents against important viruses. Only the 2,6-diaminopurine derivative exhibited moderate activity against vesicular stomatitis virus.

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CCDC-689835 contains the supplementary crystallographic data for this paper. These data can be obtained free of charge at www.ccdc.cam.ac.uk/conts/retrieving.html [or from the Cambridge Crystallographic Data Centre, 12, Union Road, Cambridge CB2 1EZ, UK; fax: +44 1223 336 033; E-mail: deposit@ccdc.cam.ac.uk.