7-Azaindole: A Versatile Scaffold for Developing Kinase Inhibitors

Chem Pharm Bull (Tokyo). 2018;66(1):29-36. doi: 10.1248/cpb.c17-00380.

Abstract

The majority of kinase inhibitors have been developed as ATP competitors to interact with a hinge region in ATP binding sites of kinases. 7-Azaindole has been found as an excellent hinge binding motif by making two hydrogen bonds with the kinase hinge region. Vemurafenib, a B-RAF kinase (serine-threonine kinase [STK]) inhibitor approved by the U.S. Food and Drug Administration (FDA) for the treatment of melanoma, was created from this simple 7-azaindole fragment by successful use of structure-based drug design techniques. The huge potential of 7-azaindole as a hinge-binding motif has encouraged many researchers to employ it as a kinase privileged fragment. This paper will review recent examples of 7-azaindole-based kinase inhibitors, and discusses their binding interactions with the kinase hinge regions.

Keywords: azaindole; fragment-based drug discovery; hinge binder; kinase inhibitor.

Publication types

  • Review

MeSH terms

  • Animals
  • Humans
  • Indoles / chemistry*
  • Indoles / pharmacology*
  • Protein Kinase Inhibitors / chemical synthesis*
  • Protein Kinase Inhibitors / chemistry
  • Protein Kinase Inhibitors / pharmacology*
  • Protein Serine-Threonine Kinases / antagonists & inhibitors*
  • Protein Serine-Threonine Kinases / metabolism

Substances

  • 7-azaindole dimer
  • Indoles
  • Protein Kinase Inhibitors
  • Protein Serine-Threonine Kinases