Enhanced FTase activity achieved via piperazine interaction with catalytic zinc

Bioorg Med Chem Lett. 2006 Feb 15;16(4):984-8. doi: 10.1016/j.bmcl.2005.10.090. Epub 2005 Nov 16.

Abstract

Benzocycloheptapyridine tricyclic compounds with piperazine or substituted piperidine moieties extending either from the 5- or 6-position of the tricyclic bridgehead exhibited enhanced FTase activity: this resulted from favorable binding of the ligand nitrogen with the catalytic zinc found in the FTase. A single isomer at C-11 with piperazine adduct extending from the 6-position, compound 24, exhibited excellent FTase activity with IC50 = 0.007 microM, soft agar IC50 = 72 nM, and Rat AUC(PO, 10 mpk) = 4.0 microM x h. X-ray of (-)-[8-chloro-6-(1-piperazinyl)-1H-benzo[5,6]]cyclohepta[1,2-b]pyridine-11-yl]-1-(methylsulfonyl)piperidine 24 bound to Ftase revealed favorable interaction between piperazine nitrogen and catalytic zinc atom.

MeSH terms

  • Alkyl and Aryl Transferases / antagonists & inhibitors
  • Alkyl and Aryl Transferases / chemistry*
  • Binding Sites / drug effects
  • Catalysis / drug effects
  • Crystallography, X-Ray
  • Ligands
  • Models, Molecular
  • Molecular Structure
  • Organometallic Compounds / chemistry*
  • Organometallic Compounds / pharmacology
  • Piperazine
  • Piperazines / chemistry*
  • Stereoisomerism
  • Structure-Activity Relationship
  • Zinc / chemistry*

Substances

  • Ligands
  • Organometallic Compounds
  • Piperazines
  • Piperazine
  • Alkyl and Aryl Transferases
  • p21(ras) farnesyl-protein transferase
  • Zinc