3-Glucosylated 5-amino-1,2,4-oxadiazoles: synthesis and evaluation as glycogen phosphorylase inhibitors

• Marion Donnier-Maréchal,
• David Goyard,
• Vincent Folliard,
• Tibor Docsa,
• Pal Gergely,
• Jean-Pierre Praly and
• Sébastien Vidal

Beilstein J. Org. Chem. 2015, 11, 499–503, doi:10.3762/bjoc.11.56

• phosphorylase; oxadiazole; Vilsmeier salt; Introduction Glycogen phosphorylase (GP) is a homodimeric enzyme that is responsible for the depolymerization of glycogen into glucose-1-phosphate, which is further converted into glucose delivered into the blood stream [1][2]. The control of GP activity could find

• corresponding amine at room temperature in dichloromethane [31] was sufficient for ureas 2a,c–e, heating (40 °C) and the addition of triethylamine [32] were required for condensation with N-methylbenzylamine to obtain urea 2b. The Vilsmeier salt was then generated in situ with oxalyl chloride from the