title: 3-Glucosylated 5-amino-1,2,4-oxadiazoles: synthesis and evaluation as glycogen phosphorylase inhibitors.
abstract: Glycogen phosporylase (GP) is a promising target for the control of glycaemia. The design of inhibitors binding at the catalytic site has been accomplished through various families of glucose-based derivatives such as oxadiazoles. Further elaboration of the oxadiazole aromatic aglycon moiety is now reported with 3-glucosyl-5-amino-1,2,4-oxadiazoles synthesized by condensation of a C-glucosyl amidoxime with N,N'-dialkylcarbodiimides or Vilsmeier salts. The 5-amino group introduced on the oxadiazole scaffold was expected to provide better inhibition of GP through potential additional interactions with the enzyme's catalytic site; however, no inhibition was observed at 625 µM.
authors.affiliation: Institut de Chimie et Biochimie Moléculaires et Supramoléculaires (UMR 5246), Laboratoire de Chimie Organique 2, Université Claude Bernard Lyon 1 and CNRS; 43 Boulevard du 11 Novembre 1918, F-69622, Villeurbanne, France.
authors.forename: Marion
authors.initials: M
authors.lastname: Donnier-Maréchal
authors.affiliation: Institut de Chimie et Biochimie Moléculaires et Supramoléculaires (UMR 5246), Laboratoire de Chimie Organique 2, Université Claude Bernard Lyon 1 and CNRS; 43 Boulevard du 11 Novembre 1918, F-69622, Villeurbanne, France.
authors.forename: David
authors.initials: D
authors.lastname: Goyard
authors.affiliation: Institut de Chimie et Biochimie Moléculaires et Supramoléculaires (UMR 5246), Laboratoire de Chimie Organique 2, Université Claude Bernard Lyon 1 and CNRS; 43 Boulevard du 11 Novembre 1918, F-69622, Villeurbanne, France.
authors.forename: Vincent
authors.initials: V
authors.lastname: Folliard
authors.affiliation: Department of Medical Chemistry, Faculty of Medicine, University of Debrecen, Egyetem tér 1, H-4032 Debrecen, Hungary.
authors.forename: Tibor
authors.initials: T
authors.lastname: Docsa
authors.affiliation: Department of Medical Chemistry, Faculty of Medicine, University of Debrecen, Egyetem tér 1, H-4032 Debrecen, Hungary.
authors.forename: Pal
authors.initials: P
authors.lastname: Gergely
authors.affiliation: Institut de Chimie et Biochimie Moléculaires et Supramoléculaires (UMR 5246), Laboratoire de Chimie Organique 2, Université Claude Bernard Lyon 1 and CNRS; 43 Boulevard du 11 Novembre 1918, F-69622, Villeurbanne, France.
authors.forename: Jean-Pierre
authors.initials: JP
authors.lastname: Praly
authors.affiliation: Institut de Chimie et Biochimie Moléculaires et Supramoléculaires (UMR 5246), Laboratoire de Chimie Organique 2, Université Claude Bernard Lyon 1 and CNRS; 43 Boulevard du 11 Novembre 1918, F-69622, Villeurbanne, France.
authors.forename: Sébastien
authors.initials: S
authors.lastname: Vidal
keywords: Vilsmeier salt; amidoxime; carbodiimide; glycogen phosphorylase; oxadiazole