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Synthesis of Substituted Imidazolo[1,2‐ a ]piperidinoses and Their Evaluation as Glycosidase Inhibitors
Author(s) -
Dubost Estelle,
Le Nouën Didier,
Streith Jacques,
Tarnus Céline,
Tschamber Théophile
Publication year - 2006
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200500414
Subject(s) - chemistry , moiety , imidazole , stereochemistry , hydroxymethyl
The synthesis of substituted imidazolo[1,2‐ a ]‐ L ‐ arabino ‐piperidinoses is reported. The substituents are methyl, phenylmethyl, phenylethyl, cyclohexylethyl, pyridinylethyl, piperidinylethyl, phenylpropyl and hydroxymethyl. All substituents are connected to the imidazole moiety. Examination of the inhibitory properties of the newly synthesised compounds against a β‐glucosidase (from almonds) and a β‐galactosidase (from Escherichia coli ) lead to the conclusion that the substitution of the C‐2 position on the imidazole moiety with cyclohexylethyl or phenylethyl gives the best results ( K i = 2 and 4 n M , respectively, against a β‐galactosidase) as compared with the non‐substituted azasugar. The synthesis of the imidazolo[1,2‐ a ]‐ D ‐ xylo ‐piperidinose substituted with phenylethyl is also reported, as well as its inhibitory potency against the β‐xylosidase from Aspergillus niger .(© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2006)