Novel 1,2-Disubstituted Carbocyclic Nucleoside Analogues of Purine with a Cyclopentene Ring

P.  Besada; M. J.  González-Moa; C.  Terán; L.  Santana; E.  Uriarte

doi:10.1055/s-2002-35239

PAPER

Novel 1,2-Disubstituted Carbocyclic Nucleoside Analogues of Purine with a Cyclopentene Ring

P. Besada^a, M. J. González-Moa^a, C. Terán*^a, L. Santana^b, E. Uriarte^b
^a Departamento de Química Orgánica, Facultad de Ciencias, Universidad de Vigo, 36200 Vigo, Spain
Fax: +34(986)812 262; e-Mail: mcteran@uvigo.es;
^b Departamento de Química Orgánica, Facultad de Farmacia, Universidad de Santiago de Compostela, 15782 Santiago de Compostela, Spain

Abstract

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Abstract

A total and versatile synthesis of a new series of carbocyclic nucleoside analogues which are derivatives of purine with a 1,2-disubstituted cyclopentene ring (I) is described. The 6-chloropurine derivatives 3 and 9 were prepared by construction of the heterocyclic base about the primary amino group of the (±)-cis-2-amino-3-cyclopentenylmethanol (1), which was synthesized in good yield from cyclopentadiene in four steps. The substitution of a chlorine atom in the compounds 3 and 9 by an amino group (compounds 4 and 10) and by a hydroxyl group (compounds 5 and 11) was carried out with NH₄OH or with NaOH, respectively.

Key words

amino alcohol - nucleosides - heterocycles - cyclization - nucleophilic aromatic substitution

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Referenzen

References

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