The discovery of novel benzofuran-2-carboxylic acids as potent Pim-1 inhibitors

Bioorg Med Chem Lett. 2011 May 15;21(10):3050-6. doi: 10.1016/j.bmcl.2011.03.030. Epub 2011 Mar 16.

Abstract

Novel benzofuran-2-carboxylic acids, exemplified by 29, 38 and 39, have been discovered as potent Pim-1 inhibitors using fragment based screening followed by X-ray structure guided medicinal chemistry optimization. The compounds demonstrate potent inhibition against Pim-1 and Pim-2 in enzyme assays. Compound 29 has been tested in the Ambit 442 kinase panel and demonstrates good selectivity for the Pim kinase family. X-ray structures of the inhibitor/Pim-1 binding complex reveal important salt-bridge and hydrogen bond interactions mediated by the compound's carboxylic acid and amino groups.

MeSH terms

  • Animals
  • Benzofurans / chemistry*
  • Carboxylic Acids / chemical synthesis
  • Carboxylic Acids / chemistry
  • Carboxylic Acids / pharmacology*
  • Crystallography, X-Ray
  • Enzyme Activation / drug effects*
  • Enzyme Inhibitors / chemical synthesis
  • Enzyme Inhibitors / chemistry
  • Enzyme Inhibitors / pharmacology*
  • Humans
  • Inhibitory Concentration 50
  • Microsomes, Liver / drug effects
  • Microsomes, Liver / enzymology
  • Models, Molecular
  • Molecular Structure
  • Proto-Oncogene Proteins c-pim-1 / antagonists & inhibitors*
  • Rats

Substances

  • Benzofurans
  • Carboxylic Acids
  • Enzyme Inhibitors
  • Proto-Oncogene Proteins c-pim-1