A practical synthesis of m-prostaglandin E synthase-1 inhibitor MK-7285

J Org Chem. 2009 Oct 16;74(20):7790-7. doi: 10.1021/jo901798d.

Abstract

A practical, kilogram-scale chromatography-free synthesis of mPGE synthase I inhibitor MK-7285 is described. The route features a convergent assembly of the core phenanthrene unit via amide-directed ortho-metalation and proximity-induced anionic cyclization, followed by imidazole synthesis and late-stage cyanation.

MeSH terms

  • Cyclization
  • Enzyme Inhibitors / chemical synthesis*
  • Enzyme Inhibitors / chemistry*
  • Heterocyclic Compounds, 4 or More Rings / chemical synthesis*
  • Heterocyclic Compounds, 4 or More Rings / chemistry*
  • Intramolecular Oxidoreductases / chemistry*
  • Molecular Structure
  • Prostaglandin-E Synthases

Substances

  • Enzyme Inhibitors
  • Heterocyclic Compounds, 4 or More Rings
  • MK-7285
  • Intramolecular Oxidoreductases
  • Prostaglandin-E Synthases