Please use this identifier to cite or link to this item: http://hdl.handle.net/10261/37531
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Title: 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
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
URI: http://hdl.handle.net/10261/37531
ISSN: 0022-3263
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Citation: Journal of Organic Chemistry 74(9): 3595-3598 (2009)
References: 19334717
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