The synthesis of substituted bipiperidine amide compounds as CCR3 ligands: antagonists versus agonists

Bioorg Med Chem Lett. 2005 Jun 15;15(12):3020-3. doi: 10.1016/j.bmcl.2005.04.054.

Abstract

Structure-activity relationship study of bipiperidine amide 1 has identified the reverse bipiperidine amide 4a as a CC chemokine-3 (CCR3) receptor antagonist. Optimization of the structure-activity relationship of compound 4a has resulted in the identification of a CCR3 antagonist 4i as well as a CCR3 agonist 13.

MeSH terms

  • Amides / chemical synthesis*
  • Amides / pharmacology*
  • Chemokine CCL11
  • Chemokines, CC / metabolism
  • Chemotactic Factors, Eosinophil / metabolism
  • Guanosine 5'-O-(3-Thiotriphosphate) / metabolism
  • Humans
  • Piperidines / chemical synthesis*
  • Piperidines / pharmacology*
  • Protein Binding
  • Receptors, CCR3
  • Receptors, Chemokine / agonists*
  • Receptors, Chemokine / antagonists & inhibitors*
  • Receptors, HIV / agonists
  • Receptors, HIV / antagonists & inhibitors
  • Structure-Activity Relationship

Substances

  • Amides
  • CCL11 protein, human
  • CCR3 protein, human
  • Chemokine CCL11
  • Chemokines, CC
  • Chemotactic Factors, Eosinophil
  • Piperidines
  • Receptors, CCR3
  • Receptors, Chemokine
  • Receptors, HIV
  • Guanosine 5'-O-(3-Thiotriphosphate)