Synthesis of heterocyclic N-(β-d-glucopyranosyl)carboxamides for inhibition of glycogen phosphorylase

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23 Citations (Scopus)


In a DCC-mediated coupling 2,3,4,6-tetra-O-acetyl-β-d- glucopyranosylamine and propiolic acid gave N-propynoyl-2,3,4,6-tetra-O-acetyl- β-d-glucopyranosylamine which was transformed by 1,3-dipolar cycloadditions with aromatic azides and nitrile-oxides to the corresponding O-peracetylated N-(β-d-glucopyranosyl)-1-substituted-1,2,3-triazole-4-carboxamides and N-(β-d-glucopyranosyl)-3-substituted-isoxazole-5-carboxamides, respectively. These compounds were O-deacetylated by Zemplén's protocol to be tested as inhibitors of rabbit muscle glycogen phosphorylase b. The best inhibitors of the two series were N-(β-d-glucopyranosyl)-1-(3,5-dimethyl- phenyl)-1,2,3-triazole-4-carboxamide (K i = 34 μM) and N-(β-d-glucopyranosyl)-3-(indol-2-yl)-isoxazole-5-carboxamide (K i = 164 μM).

Original languageEnglish
Pages (from-to)56-63
Number of pages8
JournalCarbohydrate Research
Publication statusPublished - Apr 1 2012


  • 1,2,3-Triazole-4-carboxamide
  • Azide-alkyne cycloaddition
  • Glycogen phosphorylase
  • Isoxazole-5-carboxamide
  • N-(β-d-Glucopyranosyl) carboxamide
  • Nitrile-oxide-alkyne cycloaddition

ASJC Scopus subject areas

  • Analytical Chemistry
  • Biochemistry
  • Organic Chemistry

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