Conformationally-locked N-glycosides with selective β-glucosidase inhibitory activity: identification of a new non-iminosugar-type pharmacological chaperone for …

…, C Ortiz Mellet, JM García Fernández…

Index: Castilla, Javier; Risquez, Rocio; Cruz, Deysi; Higaki, Katsumi; Nanba, Eiji; Ohno, Kousaku; Suzuki, Yoshiyuki; Diaz, Yolanda; Mellet, Carmen Ortiz; Fernandez, Jose M. Garcia; Castillon, Sergio Journal of Medicinal Chemistry, 2012 , vol. 55, # 15 p. 6857 - 6865

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Citation Number: 25

Abstract

A series of conformationally locked N-glycosides having a cis-1, 2-fused pyranose–1, 3- oxazoline-2-thione structure and bearing different substituents at the exocyclic sulfur has been prepared. The polyhydroxylated bicyclic system was built in only three steps by treatment of the corresponding readily available 1, 2-anhydrosugar with KSCN using TiO (TFA) 2 as catalyst, followed by S-alkylation and acetyl deprotection. In vitro screening ...