Xanthine mimetics as potent dipeptidyl peptidase IV inhibitors

Bioorg Med Chem Lett. 2006 Dec 15;16(24):6226-30. doi: 10.1016/j.bmcl.2006.09.024. Epub 2006 Sep 28.

Abstract

A series of xanthine mimetics containing 5,5 and 5,6 heterocycle fused imidazoles were synthesized as dipeptidyl peptidase IV inhibitors. Compound 7 is potent (h-DPPIV K(i)=2nM) and exhibits excellent selectivity and no species specificity against rat and human enzymes. The X-ray structure confirms that the binding mode of 7 to rat DPPIV is similar to the parent xanthines.

MeSH terms

  • Animals
  • Dipeptidyl Peptidase 4 / chemistry
  • Dipeptidyl-Peptidase IV Inhibitors*
  • Imidazoles / pharmacology
  • Kinetics
  • Models, Molecular
  • Protease Inhibitors / chemical synthesis
  • Protease Inhibitors / pharmacology*
  • Protein Conformation
  • Rats
  • Structure-Activity Relationship
  • X-Ray Diffraction
  • Xanthines / chemical synthesis
  • Xanthines / pharmacology*

Substances

  • Dipeptidyl-Peptidase IV Inhibitors
  • Imidazoles
  • Protease Inhibitors
  • Xanthines
  • Dipeptidyl Peptidase 4