Identification of pharmacokinetically stable 3, 10-dibromo-8-chlorobenzocycloheptapyridine farnesyl protein transferase inhibitors with potent enzyme and cellular activities

J Med Chem. 1999 Jul 15;42(14):2651-61. doi: 10.1021/jm990059k.

Abstract

Farnesyl protein transferase (FPT) is a promising target for the development of cancer chemotherapeutics because it is responsible for the farnesylation of oncogenic p21 Ras proteins which are found in nearly 30% of all human cancers and necessary for cellular development and growth. The recent discovery and progression to phase II clinical trials of trihalobenzocycloheptapyridine Sch-66336 as a potent inhibitor of FPT with oral, in vivo efficacy in mice have spawned extensive structure-activity relationship studies (SAR) of this class of compounds. Of the many trihalobenzocycloheptapyridine analogues prepared, we have identified several which inhibit FPT and cellular proliferation at single-digit nanomolar concentrations and which have good pharmacokinetic properties in mice.

MeSH terms

  • Administration, Oral
  • Alkyl and Aryl Transferases / antagonists & inhibitors*
  • Animals
  • Biological Availability
  • COS Cells
  • Cell Division / drug effects
  • Enzyme Inhibitors / chemical synthesis*
  • Enzyme Inhibitors / chemistry
  • Enzyme Inhibitors / pharmacokinetics
  • Haplorhini
  • Mice
  • Mice, Nude
  • Piperidines / chemical synthesis*
  • Piperidines / chemistry
  • Piperidines / pharmacokinetics
  • Protein Prenylation
  • Proto-Oncogene Proteins p21(ras) / metabolism
  • Pyridines / chemical synthesis*
  • Pyridines / chemistry
  • Pyridines / pharmacokinetics
  • Structure-Activity Relationship
  • Sulfonamides / chemical synthesis*
  • Sulfonamides / chemistry
  • Sulfonamides / pharmacokinetics
  • Sulfonylurea Compounds / chemical synthesis*
  • Sulfonylurea Compounds / chemistry
  • Sulfonylurea Compounds / pharmacokinetics

Substances

  • Enzyme Inhibitors
  • Piperidines
  • Pyridines
  • Sulfonamides
  • Sulfonylurea Compounds
  • Alkyl and Aryl Transferases
  • p21(ras) farnesyl-protein transferase
  • Proto-Oncogene Proteins p21(ras)
  • lonafarnib