Aryl tetrahydropyridine inhibitors of farnesyltransferase: glycine, phenylalanine and histidine derivatives

Bioorg Med Chem Lett. 2003 Apr 7;13(7):1359-62. doi: 10.1016/s0960-894x(03)00095-7.

Abstract

Inhibitors of farnesyltransferase are effective against a variety of tumors in mouse models of cancer. Clinical trials to evaluate these agents in humans are ongoing. In our effort to develop new farnesyltransferase inhibitors, we have discovered a series of aryl tetrahydropyridines that incorporate substituted glycine, phenylalanine and histidine residues. The design, synthesis, SAR and biological properties of these compounds will be discussed.

Publication types

  • Research Support, Non-U.S. Gov't
  • Research Support, U.S. Gov't, Non-P.H.S.

MeSH terms

  • Alkyl and Aryl Transferases / antagonists & inhibitors*
  • Biological Availability
  • Crystallography, X-Ray
  • Enzyme Inhibitors / chemical synthesis*
  • Enzyme Inhibitors / pharmacokinetics
  • Enzyme Inhibitors / pharmacology*
  • Farnesyltranstransferase
  • Genes, ras / drug effects
  • Glycine / analogs & derivatives*
  • Glycine / pharmacology
  • Histidine / analogs & derivatives*
  • Histidine / pharmacology
  • Models, Molecular
  • Molecular Conformation
  • Phenylalanine / analogs & derivatives*
  • Phenylalanine / pharmacology
  • Pyridines / chemical synthesis*
  • Pyridines / pharmacology*
  • Structure-Activity Relationship

Substances

  • Enzyme Inhibitors
  • Pyridines
  • Phenylalanine
  • Histidine
  • Alkyl and Aryl Transferases
  • geranylgeranyltransferase type-I
  • Farnesyltranstransferase
  • Glycine

Associated data

  • PDB/1N94
  • PDB/1N95