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Please use this identifier to cite or link to this item: http://hdl.handle.net/10261/36185
Title: Synthesis and evaluation of sulfamide-type indolizidines as glycosidase inhibitors
Authors: Benltifa, Mahmoud; García Moreno, María Isabel; Ortiz-Mellet, Carmen; García-Fernández, José Manuel; Wadouachi, Anne
Keywords: Cyclic sulfamide
Mannosidases inhibitor
Issue Date: 4-Apr-2008
Publisher: Elsevier
Citation: Bioorganic and Medicinal Chemistry Letters 18(9): 2805-2808 (2008)
Abstract: A practical synthesis of reducing sulfamide-derived iminosugar glycomimetics related to the indolizidine glycosidase inhibitor family is reported. The polyhydroxylated bicyclic system was built from readily accessible hexofuranose derivatives through a synthetic scheme that involves 5,6-cyclic sulfamides. Further intramolecular nucleophilic addition of the sulfamide nitrogen atom to the masked aldehyde group of the monosaccharide in the open chain form afforded the target sugar mimics. By starting from d-glucose and d-mannose precursors, 2-aza-3,3-dioxo-3-thiaindolizidine derivatives with hydroxylation profiles that matched those of (+)-castanospermine and 6-epi-(+)-castanospermine were obtained. In vitro screening against a panel of glycosidases evidenced a high selectivity towards α-mannosidase
Description: 4 páginas, 3 figuras, 2 esquemas
Publisher version (URL): http://dx.doi.org/10.1016/j.bmcl.2008.04.004
URI: http://hdl.handle.net/10261/36185
DOI: 10.1016/j.bmcl.2008.04.004
ISSN: 0960-894X
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