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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.
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https://hal-udl.archives-ouvertes.fr/hal-02123939
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Submitted on : Thursday, May 9, 2019 - 10:47:23 AM
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Marion Donnier-Marechal, David Goyard, Vincent Folliard, Tibor Docsa, Pál Gergely, et al.. 3-Glucosylated 5-amino-1,2,4-oxadiazoles: synthesis and evaluation as glycogen phosphorylase inhibitors. Beilstein Journal of Organic Chemistry, Beilstein-Institut, 2015, 11, pp.499-503. ⟨10.3762/bjoc.11.56⟩. ⟨hal-02123939⟩

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