Synthesis, biological evaluation and structural determination of beta-aminoacyl-containing cyclic hydrazine derivatives as dipeptidyl peptidase IV (DPP-IV) inhibitors

Bioorg Med Chem Lett. 2007 May 1;17(9):2622-8. doi: 10.1016/j.bmcl.2007.01.111. Epub 2007 Feb 8.

Abstract

Inhibitors of dipeptidyl peptidase IV (DPP-IV) have been shown to be effective treatments for type 2 diabetes. A series of beta-aminoacyl-containing cyclic hydrazine derivatives were synthesized and evaluated as DPP-IV inhibitors. One member of this series, (R)-3-amino-1-(2-benzoyl-1,2-diazepan-1-yl)-4-(2,4,5-trifluorophenyl)butan-1-one (10f), showed potent in vitro activity, good selectivity and in vivo efficacy in mouse models. Also, the binding mode of compound 10f was determined by X-ray crystallography.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Chemistry, Pharmaceutical / methods*
  • Crystallography, X-Ray
  • Dipeptidyl-Peptidase IV Inhibitors*
  • Drug Design
  • Enzyme Inhibitors / chemical synthesis*
  • Enzyme Inhibitors / pharmacology*
  • Glucagon-Like Peptide 1 / metabolism
  • Hydrazines / chemical synthesis*
  • Hydrazines / pharmacology
  • Inhibitory Concentration 50
  • Kinetics
  • Mice
  • Mice, Inbred C57BL
  • Models, Chemical
  • Molecular Conformation
  • Protein Structure, Tertiary

Substances

  • Dipeptidyl-Peptidase IV Inhibitors
  • Enzyme Inhibitors
  • Hydrazines
  • hydrazine
  • Glucagon-Like Peptide 1