Synthesis of C-xylopyranosyl- and xylopyranosylidene-spiro-heterocycles as potential inhibitors of glycogen phosphorylase

László Somsák, Éva Bokor, Beáta Czibere, Katalin Czifrák, Csenge Koppány, László Kulcsár, Sándor Kun, Eniko Szilágyi, Marietta Tóth, Tibor Docsa, Pál Gergely

Research output: Article

14 Citations (Scopus)

Abstract

New derivatives of d-xylose with aglycons of the most efficient glucose derived inhibitors of glycogen phosphorylase were synthesized to explore the specificity of the enzyme towards the structure of the sugar part of the molecules. Thus, 2-(β-d-xylopyranosyl)benzimidazole and 3-substituted-5-(β-d-xylopyranosyl)-1,2,4-triazoles were obtained in multistep procedures from O-perbenzoylated β-d-xylopyranosyl cyanide. Cycloadditions of nitrile-oxides and O-peracetylated exo-xylal obtained from the corresponding β-d-xylopyranosyl cyanide furnished xylopyranosylidene-spiro-isoxazoline derivatives. Oxidative ring closure of O-peracetylated β-d-xylopyranosyl-thiohydroximates prepared from 1-thio-β-d-xylopyranose and nitrile-oxides gave xylopyranosylidene-spiro-oxathiazoles. The fully deprotected test compounds were assayed against rabbit muscle glycogen phosphorylase b to show moderate inhibition for 3-(2-naphthyl)-5-(β-d-xylopyranosyl)-1,2,4-triazole (IC50 = 0.9 mM) only.

Original languageEnglish
Pages (from-to)38-48
Number of pages11
JournalCarbohydrate Research
Volume399
DOIs
Publication statusPublished - nov. 18 2014

ASJC Scopus subject areas

  • Analytical Chemistry
  • Biochemistry
  • Organic Chemistry

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