Synthesis and evaluation of novel 3,4,6-substituted 2-quinolones as FMS kinase inhibitors

Bioorg Med Chem Lett. 2008 Mar 15;18(6):2097-102. doi: 10.1016/j.bmcl.2008.01.088. Epub 2008 Jan 30.

Abstract

A series of 3,4,6-substituted 2-quinolones has been synthesized and evaluated as inhibitors of the kinase domain of macrophage colony-stimulating factor-1 receptor (FMS). The fully optimized compound, 4-(4-ethyl-phenyl)-3-(2-methyl-3H-imidazol-4-yl)-2-quinolone-6-carbonitrile 21b, has an IC(50) of 2.5 nM in an in vitro assay and 5.0 nM in a bone marrow-derived macrophage cellular assay. Inhibition of FMS signaling in vivo was also demonstrated in a mouse pharmacodynamic model.

Publication types

  • Evaluation Study

MeSH terms

  • Administration, Oral
  • Animals
  • Biological Availability
  • Cell Proliferation / drug effects
  • Fluorescence Polarization
  • Genes, fos / genetics
  • Macrophage Colony-Stimulating Factor / metabolism
  • Macrophages / drug effects*
  • Mice
  • Mice, Inbred C57BL
  • Molecular Structure
  • Protein Kinase Inhibitors / chemical synthesis*
  • Protein Kinase Inhibitors / pharmacology*
  • Quinolones / chemical synthesis*
  • Quinolones / pharmacokinetics
  • Quinolones / pharmacology*
  • RNA, Messenger / genetics
  • RNA, Messenger / metabolism
  • Rats
  • Receptor, Macrophage Colony-Stimulating Factor / antagonists & inhibitors*
  • Receptor, Macrophage Colony-Stimulating Factor / metabolism
  • Reverse Transcriptase Polymerase Chain Reaction
  • Spleen / metabolism
  • Structure-Activity Relationship

Substances

  • 4-(4-ethyl-phenyl)-3-(2-methyl-3H-imidazol-4-yl)-2-quinolone-6-carbonitrile
  • Protein Kinase Inhibitors
  • Quinolones
  • RNA, Messenger
  • Macrophage Colony-Stimulating Factor
  • Receptor, Macrophage Colony-Stimulating Factor