The discovery of tropane-derived CCR5 receptor antagonists

Chem Biol Drug Des. 2006 Apr;67(4):305-8. doi: 10.1111/j.1747-0285.2006.00376.x.

Abstract

The development of compound 1, a piperidine-based CCR5 receptor antagonist with Type I CYP2D6 inhibition, into the tropane-derived analogue 5, is described. This compound, which is devoid of CYP2D6 liabilities, is a highly potent ligand for the CCR5 receptor and has broad-spectrum activity against a range of clinically relevant HIV isolates. The identification of human ether a-go-go-related gene channel inhibition within this series is described and the potential for QTc interval prolongation discussed. Furthermore, structure activity relationship (SAR) around the piperidine moiety is also described.

Publication types

  • Letter

MeSH terms

  • Anti-HIV Agents / chemical synthesis
  • Anti-HIV Agents / chemistry*
  • Anti-HIV Agents / pharmacology
  • CCR5 Receptor Antagonists*
  • Cytochrome P-450 CYP2D6 Inhibitors
  • HIV-1 / drug effects
  • Humans
  • Models, Molecular
  • Piperidines / chemistry
  • Receptors, CCR5 / metabolism
  • Structure-Activity Relationship
  • Tropanes / chemical synthesis
  • Tropanes / chemistry*
  • Tropanes / pharmacology

Substances

  • Anti-HIV Agents
  • CCR5 Receptor Antagonists
  • Cytochrome P-450 CYP2D6 Inhibitors
  • Piperidines
  • Receptors, CCR5
  • Tropanes
  • piperidine