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Closed Access item Synthesis and biological evaluation of 6-oxa-nor-tropane glycomimetics as glycosidase inhibitors

Authors:García Moreno, María Isabel
Ortiz-Mellet, Carmen
García-Fernández, José Manuel
Keywords:Calystegines, Glycosidase inhibitors
Issue Date:26-May-2007
Citation:Tetrahedron 63(33): 7879-7884 (2007)
Abstract: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.
Description:6 páginas, esquemas.
Publisher version (URL):http://dx.doi.org/10.1016/j.tet.2007.05.085
Appears in Collections:(IIQ) Artículos

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