Structure-based design and subsequent optimization of 2-tolyl-(1,2,3-triazol-1-yl-4-carboxamide) inhibitors of p38 MAP kinase

Bioorg Med Chem Lett. 2008 Jun 1;18(11):3251-5. doi: 10.1016/j.bmcl.2008.04.043. Epub 2008 Apr 25.

Abstract

A computer-aided drug design strategy leads to the identification of a new class of p38 inhibitors based on the 2-tolyl-(1,2,3-triazol-1-yl-4-carboxamide) scaffold. The tolyl triazole amides provided a potent platform amenable to optimization. Further exploration leads to compounds with greater than 100-fold improvement in binding affinity to p38. Derivatives prepared to alter the physicochemical properties produced inhibitors with IC(50)'s in human whole blood as low as 83 nM.

MeSH terms

  • Binding Sites
  • Computer-Aided Design
  • Drug Design*
  • Enzyme Inhibitors / blood
  • Enzyme Inhibitors / chemical synthesis*
  • Enzyme Inhibitors / chemistry
  • Enzyme Inhibitors / pharmacology*
  • Humans
  • Inhibitory Concentration 50
  • Molecular Structure
  • Structure-Activity Relationship
  • Triazoles / blood
  • Triazoles / chemical synthesis*
  • Triazoles / chemistry
  • Triazoles / pharmacology*
  • p38 Mitogen-Activated Protein Kinases / antagonists & inhibitors*

Substances

  • Enzyme Inhibitors
  • Triazoles
  • p38 Mitogen-Activated Protein Kinases