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Synthesis 2008(12): 1845-1852  
DOI: 10.1055/s-2008-1067091
PAPER
© Georg Thieme Verlag Stuttgart · New York

Synthesis and Antiviral Activities of Novel Purinyl- and Pyrimidinyl­carbanucleosides Derived from Indan [1]

Nerea Alonsoa, Olga Caamañoa, Franco Fernándeza, Xerardo García-Mera*a, Melvin Moralesa, José Enrique Rodríguez-Borgesb, Eric De Clercqc
a Departamento de Química Orgánica, Facultade de Farmacia, Universidade de Santiago de Compostela, 15782 Santiago de Compostela, Spain
Fax: +34(981)594912; e-Mail: qoxgmera@usc.es;
b CIQ, Departamento de Química, Universidade do Porto, Rua do Campo Alegre 687, 4169-007 Porto, Portugal
c Rega Institute for Medical Research, Katholieke Universiteit Leuven, 3000 Leuven, Belgium
Further Information

Publication History

Received 7 February 2008
Publication Date:
16 May 2008 (online)

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Abstract

Starting from (±)-trans- and (±)-cis-3-hydroxymethyl-1-indanol, novel 6-substituted purinylcarbanucleoside derivatives of indan were synthesised through a key coupling reaction with 6-chloropurine under Mitsunobu conditions. Suzuki-Miyaura reactions of the protected 6-chloropurine derivative with different arylboronic­ acids afforded the corresponding 6-arylpurinylcarba­nucleoside derivatives. Finally, three new 5-halouracilcarbanucleosides were prepared by the reaction of a uracilcarbanucleoside with different N-halosuccinimides. All of the new analogues were evaluated for antiviral activity against a wide variety of viruses.

Key words

synthesis - indan carbanucleosides - Mitsunobu reaction - Suzuki-Miyaura reaction - antiviral activity

1

Part of this work was presented at the XIV Congreso Nacional of The Sociedad Española de Química Terapéutica, Bilbao: Spain, September 2005.

1

Part of this work was presented at the XIV Congreso Nacional of The Sociedad Española de Química Terapéutica, Bilbao: Spain, September 2005.