CCR5 receptor antagonists: discovery and SAR of novel 4-hydroxypiperidine derivatives

Bioorg Med Chem Lett. 2007 Apr 1;17(7):1883-7. doi: 10.1016/j.bmcl.2007.01.050. Epub 2007 Jan 25.

Abstract

The guanylhydrazone of 2-(4-chlorobenzyloxy)-5-bromobenzaldehyde, 1, with an IC(50) of 840 nM against the CCR5 receptor was identified using high-throughput screening. Optimization efforts led to the discovery of a novel piperidine series of CCR5 antagonists. In particular, the 4-hydroxypiperidine derivative, 6k, had improved potency against CCR5, and was a starting point for further optimization. SAR elaboration using parallel synthesis led to the identification of 10h, a potent CCR5 antagonist with an IC(50) of 11 nM.

MeSH terms

  • Animals
  • CCR5 Receptor Antagonists*
  • Cell Line
  • Chemistry, Pharmaceutical / methods*
  • Drug Design
  • Humans
  • Inhibitory Concentration 50
  • Models, Chemical
  • Molecular Conformation
  • Molecular Structure
  • Piperidines / chemical synthesis
  • Piperidines / chemistry*
  • Piperidines / pharmacology
  • Rats
  • Structure-Activity Relationship
  • Time Factors
  • Transfection

Substances

  • CCR5 Receptor Antagonists
  • Piperidines