Antitumor 8-chlorobenzocycloheptapyridines: a new class of selective, nonpeptidic, nonsulfhydryl inhibitors of ras farnesylation

Bioorg Med Chem. 1997 Jan;5(1):93-9. doi: 10.1016/s0968-0896(96)00205-2.

Abstract

Ras farnesylation by farnesyl protein transferase (FPT) is an intracellular event that facilitates the membrane association of the ras protein and is involved in the signal transduction process. FPT inhibition could be a novel, noncytotoxic method of treating ras dependent tumor growth. We report here three structural classes of 8-chlorobenzocycloheptapyridines as novel, nonpeptidic, nonsulfhydryl FPT inhibitors having antitumor activity in mice when dosed orally. We discuss structural and conformational aspects of these compounds in relation to biological activities as well as a comparison to the conformation of a bound tetrapeptide FPT inhibitor.

MeSH terms

  • Animals
  • Antineoplastic Agents / chemistry
  • Antineoplastic Agents / pharmacokinetics
  • Antineoplastic Agents / pharmacology*
  • Benzazepines / chemistry
  • Benzazepines / pharmacokinetics
  • Benzazepines / pharmacology
  • Humans
  • Magnetic Resonance Spectroscopy
  • Mass Spectrometry
  • Mice
  • Piperidines / chemistry
  • Piperidines / pharmacokinetics
  • Piperidines / pharmacology
  • Pyridines / chemistry
  • Pyridines / pharmacokinetics
  • Pyridines / pharmacology
  • Tumor Cells, Cultured

Substances

  • Antineoplastic Agents
  • Benzazepines
  • Piperidines
  • Pyridines
  • SCH 44342