Indolin-2-one p38α inhibitors III: bioisosteric amide replacement

Bioorg Med Chem Lett. 2011 Nov 1;21(21):6253-7. doi: 10.1016/j.bmcl.2011.09.006. Epub 2011 Sep 10.

Abstract

Crystallographic structural information was used in the design and synthesis of a number of bioisosteric derivatives to replace the amide moiety in a lead series of p38α inhibitors which showed general hydrolytic instability in human liver preparations. Triazole derivative 13 was found to have moderate bioavailability in the rat and demonstrated potent in-vivo activity in an acute model of inflammation.

MeSH terms

  • Amides / chemistry*
  • Animals
  • Hydrogen Bonding
  • Indoles / chemistry
  • Indoles / pharmacokinetics
  • Indoles / pharmacology*
  • Protein Kinase Inhibitors / chemistry
  • Protein Kinase Inhibitors / pharmacology*
  • Rats
  • p38 Mitogen-Activated Protein Kinases / antagonists & inhibitors*

Substances

  • Amides
  • Indoles
  • Protein Kinase Inhibitors
  • indolin-2-one
  • p38 Mitogen-Activated Protein Kinases