Flexible synthesis and biological evaluation of novel 5-deoxyadenophorine analogues.
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.
Pearson
Morwenna S M
MS
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.
Saad
Rim Ouled
RO
Dintinger
Thierry
T
Amri
Hassen
H
Mathé-Allainmat
Monique
M
Lebreton
Jacques
J
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
C484615:5-deoxyadenophorine; D004791:Enzyme Inhibitors; D050111:Imino Sugars; D005696:Galactosidases; D005959:Glucosidases; D008361:Mannosidases; D005944:Glucosamine