Design of 1-piperazinyl-4-arylphthalazines as potent Smoothened antagonists

Bioorg Med Chem Lett. 2010 Jun 15;20(12):3618-22. doi: 10.1016/j.bmcl.2010.04.110. Epub 2010 Apr 28.

Abstract

The Hedgehog (Hh) signaling pathway regulates cell proliferation and differentiation in developing tissues, and abnormal activation of the Hh pathway has been linked to several tumor subsets. As a transducer of Hh signaling, the GPCR-like protein Smoothened (Smo) is a promising target for disruption of unregulated Hh signaling. A series of 1-amino-4-arylphthalazines was developed as potent and orally bioavailable inhibitors of Smo. A representative compound from this class demonstrated significant tumor volume reduction in a mouse medulloblastoma model.

MeSH terms

  • Administration, Oral
  • Animals
  • Biological Availability
  • Cell Line, Tumor
  • Cytochrome P-450 Enzyme System / drug effects
  • Drug Design
  • Hedgehog Proteins
  • Humans
  • Medulloblastoma / drug therapy
  • Medulloblastoma / pathology
  • Mice
  • Phthalazines / chemical synthesis
  • Phthalazines / chemistry*
  • Phthalazines / pharmacology*
  • Receptors, G-Protein-Coupled / antagonists & inhibitors*
  • Signal Transduction
  • Smoothened Receptor

Substances

  • Hedgehog Proteins
  • Phthalazines
  • Receptors, G-Protein-Coupled
  • SMO protein, human
  • Smo protein, mouse
  • Smoothened Receptor
  • Cytochrome P-450 Enzyme System