Synthesis of 2-(β-d-glucopyranosylamino)-5-substituted-1,3,4- oxadiazoles for inhibition of glycogen phosphorylase

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Abstract

Aromatic aldehyde 4-(2,3,4,6-tetra-O-acetyl-β-d-glucopyranosyl) semicarbazones were synthesized by the addition of different hydrazones onto O-peracetylated β-d-glucopyranosyl isocyanate. Oxidative transformations of these precursors gave O-protected 2-(β-d-glucopyranosylamino)-5- substituted-1,3,4-oxadiazoles. Removal of the O-acetyl protecting groups under Zemplén conditions gave test compounds to show low micromolar inhibition against rabbit muscle glycogen phosphorylase b. Best inhibitors of these series were 4-(β-d-glucopyranosyl)semicarbazones of 4-nitrobenzaldehyde (K i = 4.5 μM), 2-naphthaldehyde (Ki = 5.5 μM) and 2-(β-d-glucopyranosylamino)-5-(4-methylphenyl)-1,3,4-oxadiazole (K i = 12 μM).

Original languageEnglish
Pages (from-to)196-204
Number of pages9
JournalCarbohydrate Research
Volume381
DOIs
Publication statusPublished - Jan 1 2013

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Keywords

  • 1,3,4-Oxadiazole
  • Glycogen phosphorylase
  • Inhibitor
  • Semicarbazone
  • β-d-Glucopyranosyl derivatives

ASJC Scopus subject areas

  • Analytical Chemistry
  • Biochemistry
  • Organic Chemistry

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