Synthesis of a C-glucosylated cyclopropylamide and evaluation as a glycogen phosphorylase inhibitor

Philippe Bertus, Jan Szymoniak, Erwann Jeanneau, Tibor Docsa, Pál Gergely, Jean Pierre Praly, Sébastien Vidal

Research output: Article

11 Citations (Scopus)

Abstract

The synthesis of carbohydrate-based glycogen phosphorylase inhibitors is attractive for potential applications in the treatment of type 2 diabetes. A titanium-mediated synthesis led to a benzoylated C-glucosylated cyclopropylamine intermediate, which underwent a benzoyl migration to afford the corresponding 2-hydroxy-C-glycoside. X-ray crystallographic studies revealed a unit cell composed of four molecules as pairs of dimers connected through two hydrogen bonds. The deprotection of the benzoate esters under Zemplén conditions afforded a glycogen phosphorylase inhibitor candidate displaying weak inhibition toward glycogen phosphorylase (16% at 2.5 mM).

Original languageEnglish
Pages (from-to)4774-4778
Number of pages5
JournalBioorganic and Medicinal Chemistry Letters
Volume18
Issue number17
DOIs
Publication statusPublished - szept. 1 2008

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ASJC Scopus subject areas

  • Biochemistry
  • Molecular Medicine
  • Molecular Biology
  • Pharmaceutical Science
  • Drug Discovery
  • Clinical Biochemistry
  • Organic Chemistry

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