C-(2-Deoxy-d-arabino-hex-1-enopyranosyl)-oxadiazoles: Synthesis of possible isomers and their evaluation as glycogen phosphorylase inhibitors

Éva Bokor, Eszter Szennyes, Tibor Csupász, Nóra Tóth, Tibor Docsa, Pál Gergely, László Somsák

Research output: Contribution to journalArticle

15 Citations (Scopus)

Abstract

Abstract Synthetic methods were elaborated for d-glucals attached to oxadiazoles by a C-C bond. Introduction of the double bond was effected by either DBU induced elimination of PhCOOH from the O-perbenzoylated glucopyranosyl precursors or Zn/N-methylimidazole mediated reductive elimination from the 1-bromoglucopyranosyl starting compounds. Alternatively, heterocyclizations of 2-deoxy-d-arabino-hex-1-enopyranosyl cyanide were also carried out. Test compounds were obtained by Zemplén debenzoylation, however, none of them showed significant inhibition of rabbit muscle glycogen phosphorylase b.

Original languageEnglish
Article number6993
Pages (from-to)71-79
Number of pages9
JournalCarbohydrate Research
Volume412
DOIs
Publication statusPublished - Jun 14 2015

Keywords

  • C-Glycosyl compounds
  • Glycogen phosphorylase
  • Inhibitor
  • Oxadiazoles
  • d-Glucal

ASJC Scopus subject areas

  • Analytical Chemistry
  • Biochemistry
  • Organic Chemistry

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