Design, synthesis, and structure-activity relationship of substrate competitive, selective, and in vivo active triazole and thiadiazole inhibitors of the c-Jun N-terminal kinase

J Med Chem. 2009 Apr 9;52(7):1943-52. doi: 10.1021/jm801503n.

Abstract

We report comprehensive structure-activity relationship studies on a novel series of c-Jun N-terminal kinase (JNK) inhibitors. The compounds are substrate competitive inhibitors that bind to the docking site of the kinase. The reported medicinal chemistry and structure-based optimizations studies resulted in the discovery of selective and potent thiadiazole JNK inhibitors that display promising in vivo activity in mouse models of insulin insensitivity.

Publication types

  • Research Support, N.I.H., Extramural
  • Research Support, Non-U.S. Gov't

MeSH terms

  • Activating Transcription Factor 2 / metabolism
  • Animals
  • Binding Sites
  • Diabetes Mellitus, Type 2 / drug therapy
  • Drug Design
  • HeLa Cells
  • Humans
  • Hypoglycemic Agents / chemical synthesis*
  • Hypoglycemic Agents / chemistry
  • Hypoglycemic Agents / pharmacology
  • Insulin Resistance
  • JNK Mitogen-Activated Protein Kinases / antagonists & inhibitors*
  • JNK Mitogen-Activated Protein Kinases / metabolism
  • Male
  • Mice
  • Phosphorylation
  • Protein Binding
  • Structure-Activity Relationship
  • Substrate Specificity
  • Thiadiazoles / chemical synthesis*
  • Thiadiazoles / chemistry
  • Thiadiazoles / pharmacology
  • Thiazoles / chemical synthesis*
  • Thiazoles / chemistry
  • Thiazoles / pharmacology
  • Triazoles / chemical synthesis*
  • Triazoles / chemistry
  • Triazoles / pharmacology

Substances

  • 5-(5-nitrothiazol-2-ylthio)-1,3,4-thiadiazol-2-amine
  • ATF2 protein, human
  • Activating Transcription Factor 2
  • Hypoglycemic Agents
  • Thiadiazoles
  • Thiazoles
  • Triazoles
  • JNK Mitogen-Activated Protein Kinases