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Título: | Synthesis and biological evaluation of 6-oxa-nor-tropane glycomimetics as glycosidase inhibitors |
Autor: | García Moreno, María Isabel; Ortiz-Mellet, Carmen; García Fernández, José Manuel CSIC ORCID | Palabras clave: | Calystegines Glycosidase inhibitors |
Fecha de publicación: | 26-may-2007 | Editor: | Elsevier | Citación: | Tetrahedron 63(33): 7879-7884 (2007) | Resumen: | The preparation of polyhydroxylated 6-oxa-nor-tropane glycomimetics structurally related to the glycosidase inhibitor family of the calystegines is reported. The synthetic strategy involves the furanose→piperidine rearrangement of 5-deoxy-5-ureido-l-idose precursors, followed by intramolecular glycosylation involving the primary hydroxyl group. Inversion of the configuration at C-3 in the resulting 6-oxa-(+)-calystegine B2 analogue allows accessing the elusive 3-epi-6-oxa-(+)-calystegine B2 skeleton. Acid-catalyzed opening of the nor-tropane bicycle was observed, however, which could be avoided by careful neutralization of the reaction mixture. The inhibition results suggest that (+)-calystegine B2 derivatives and the corresponding C-3 epimers can be seen as glucomimetics and galactomimetics, respectively, pointing to a 1-azasugar mode of action for this family of alkaloids. | Descripción: | 6 páginas, esquemas. | Versión del editor: | http://dx.doi.org/10.1016/j.tet.2007.05.085 | URI: | http://hdl.handle.net/10261/37873 | DOI: | 10.1016/j.tet.2007.05.085 | ISSN: | 0040-4020 |
Aparece en las colecciones: | (IIQ) Artículos |
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