Pictet-Spengler based synthesis of a bisarylmaleimide glycogen synthase kinase-3 inhibitor

Org Lett. 2010 Aug 20;12(16):3700-3. doi: 10.1021/ol101405g.

Abstract

A practical synthesis of the glycogen synthase kinase-3 (GSK3) inhibitor bisarylmaleimide 1 has been accomplished employing Pictet-Spengler methodology to access the indole 7-position in preparing the benzodiazepine tricyclic fragment. A seven-step linear sequence that starts with commercially available 5-fluoroindole 7 affords the bisarylmaleimide 1 in 33% overall yield.

MeSH terms

  • Glycogen Synthase Kinase 3 / antagonists & inhibitors*
  • Indoles / chemistry*
  • Maleimides / chemical synthesis*
  • Maleimides / chemistry
  • Maleimides / pharmacology*
  • Molecular Structure

Substances

  • Indoles
  • Maleimides
  • bisarylmaleimide
  • 5-fluoroindole
  • Glycogen Synthase Kinase 3