1,3-disubstituted 4-aminopiperidines as useful tools in the optimization of the 2-aminobenzo[a]quinolizine dipeptidyl peptidase IV inhibitors

Bioorg Med Chem Lett. 2007 Jun 1;17(11):2966-70. doi: 10.1016/j.bmcl.2007.03.072. Epub 2007 Mar 25.

Abstract

In a search for novel DPP-IV inhibitors, 2-aminobenzo[a]quinolizines were identified as submicromolar HTS hits. Due to the difficult synthetic access to this compound class, 1,3-disubstituted 4-aminopiperidines were used as model compounds for optimization. The developed synthetic methodology and the SAR could be transferred to the 2-aminobenzo[a]quinolizine series, leading to highly active DPP-IV inhibitors.

MeSH terms

  • Adenosine Deaminase / chemistry
  • Adenosine Deaminase Inhibitors*
  • Dipeptidyl Peptidase 4 / chemistry
  • Dipeptidyl-Peptidase IV Inhibitors*
  • Glycoproteins / antagonists & inhibitors*
  • Glycoproteins / chemistry
  • Humans
  • Piperidines / chemical synthesis
  • Piperidines / chemistry*
  • Piperidines / pharmacology
  • Protease Inhibitors / chemical synthesis
  • Protease Inhibitors / chemistry*
  • Protease Inhibitors / pharmacology
  • Protein Conformation
  • Structure-Activity Relationship

Substances

  • Adenosine Deaminase Inhibitors
  • Dipeptidyl-Peptidase IV Inhibitors
  • Glycoproteins
  • Piperidines
  • Protease Inhibitors
  • N-aminopiperidine
  • DPP4 protein, human
  • Dipeptidyl Peptidase 4
  • Adenosine Deaminase