title: Intramolecular cyclization of alkoxyaminosugars: access to novel glycosidase inhibitor families.
abstract: We report the synthesis of two novel families of iminosugars as glycosidase inhibitors involving an intramolecular cyclization between an N-alkoxyamino group and a latent aldehyde of a reducing sugar as the key step. Using this methodology we have prepared the hitherto unknown bicyclic polyhydroxylated N-(methoxy, benzyloxy)anhydroazepanes and N-benzyloxy-d-xylonojirimycin; all these novel compounds turned out to be moderate β-glucosidase inhibitors in a pH-dependent manner.
authors.affiliation: Departamento de Química Orgánica, Facultad de Química, Universidad de Sevilla, c/Profesor García González 1, E-41012 Seville, Spain.
authors.forename: Elisa
authors.initials: E
authors.lastname: Martínez-Castro
authors.forename: Alejandro
authors.initials: A
authors.lastname: González-Benjumea
authors.forename: Óscar
authors.initials: Ó
authors.lastname: López
authors.forename: Inés
authors.initials: I
authors.lastname: Maya
authors.forename: Eleuterio
authors.initials: E
authors.lastname: Álvarez
authors.forename: José G
authors.initials: JG
authors.lastname: Fernández-Bolaños
mesh_terms: D000447:Aldehydes / Q000737:chemistry; D003500:Cyclization; D006863:Hydrogen-Ion Concentration; D050111:Imino Sugars / Q000138:chemical synthesis*; D013237:Stereoisomerism; D001617:beta-Glucosidase / Q000037:antagonists & inhibitors* / Q000737:chemistry
chemical_list: D000447:Aldehydes; D050111:Imino Sugars; D001617:beta-Glucosidase