title: Flexible synthesis and biological evaluation of novel 5-deoxyadenophorine analogues.
abstract: Adenophorine and its 5-deoxy analogue have been identified as natural iminosugars with efficient glycosidase inhibitory effects. The syntheses and biological evaluation of two new series of 5-deoxyadenophorine analogues in their racemic form are reported. The compounds 12e and 13d bearing a C11 and C7 alkyl chain, respectively, were found to be potent inhibitors of the beta-glucosidase from almond with Ki near to 60 microM. The compounds 13a,d which possess a 3,4-cis stereochemistry were efficient on glucosidases but also on the beta-galactosidase, what was not observed with the 3,4-trans series 12.
authors.affiliation: Université de Nantes, CNRS, Laboratoire de Synthèse Organique, UMR 6513, Faculté des Sciences et des Techniques, 2 rue de la Houssinière, BP 92208, 44322 Nantes Cedex 3, France.
authors.forename: Morwenna S M
authors.initials: MS
authors.lastname: Pearson
authors.forename: Rim Ouled
authors.initials: RO
authors.lastname: Saad
authors.forename: Thierry
authors.initials: T
authors.lastname: Dintinger
authors.forename: Hassen
authors.initials: H
authors.lastname: Amri
authors.forename: Monique
authors.initials: M
authors.lastname: Mathé-Allainmat
authors.forename: Jacques
authors.initials: J
authors.lastname: Lebreton
mesh_terms: D000478:Alkylation; D004791:Enzyme Inhibitors / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D005696:Galactosidases / Q000037:antagonists & inhibitors / Q000378:metabolism; D005944:Glucosamine / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D005959:Glucosidases / Q000037:antagonists & inhibitors / Q000378:metabolism; D050111:Imino Sugars / Q000737:chemistry; D008361:Mannosidases / Q000037:antagonists & inhibitors / Q000378:metabolism; D015394:Molecular Structure; D013329:Structure-Activity Relationship
chemical_list: C484615:5-deoxyadenophorine; D004791:Enzyme Inhibitors; D050111:Imino Sugars; D005696:Galactosidases; D005959:Glucosidases; D008361:Mannosidases; D005944:Glucosamine