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Closed Access item Synthesis of Thiohydantoin-Castanospermine Glycomimetics as Glycosidase Inhibitors

Authors:Aguilar Moncayo, Matilde
Ortiz-Mellet, Carmen
García-Fernández, José Manuel
García Moreno, María Isabel
Keywords:Animals, Biomimetic Materials, Carbohydrates, Enzyme Inhibitors, Indolizines, Thiohydantoins, Glycoside hydrolases
Issue Date:31-Mar-2009
Publisher:American Chemical Society
Citation:Journal of Organic Chemistry 74(9): 3595-3598 (2009)
Abstract:The preparation of bicyclic carbohydrate mimics related to (+)-castanospermine incorporating a thiohydantoin moiety is reported. The synthetic approach is compatible with molecular diversity-oriented strategies and involves alpha-azidoesters, built at the C-5/C-6 segment in gluco- or galactofuranose scaffolds, as the key precursors. Reduction to the corresponding alpha-amino ester and in situ coupling with isothiocyanates afford thioureidoester intermediates that undergo spontaneous cyclization to the corresponding hydantoins, beta-elimination, and furanose --> indolizidine rearrangement in a tandem manner. Biological evaluation of the new sp(2)-iminosugar-type glycomimetics evidenced a strong influence of the nature of the substituents at the nitrogen or oxygen atoms on the glycosidase inhibitory properties.
Description:4 páginas, 2 figuras, 1 tabla, 2 esquemas.
Publisher version (URL):http://dx.doi.org/10.1021/jo900231b
Appears in Collections:(IIQ) Artículos

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