Synthesis and SAR of tolylamine 5-HT6 antagonists

Bioorg Med Chem Lett. 2009 May 1;19(9):2409-12. doi: 10.1016/j.bmcl.2009.03.077. Epub 2009 Mar 25.

Abstract

The synthesis and SAR of tolylamines with 5-HT(6) receptor antagonist activity is presented. The amine, core aromatic, peripheral aromatic, and ether linker moieties of HTS hit 1 were modulated and the effect on potency at 5-HT(6) examined. Tolylpiperidine ether 9h was found to possess desirable pharmacokinetic (PK) properties, and was also shown to enhance cognition in the rat novel object recognition paradigm.

MeSH terms

  • Amines / chemistry*
  • Animals
  • Chemistry, Organic / methods
  • Chemistry, Pharmaceutical / methods
  • Drug Design
  • Ethers / chemistry
  • Inhibitory Concentration 50
  • Kinetics
  • Models, Chemical
  • Rats
  • Receptors, Serotonin / chemistry*
  • Serotonin Receptor Agonists / chemical synthesis*
  • Serotonin Receptor Agonists / chemistry
  • Serotonin Receptor Agonists / pharmacology
  • Structure-Activity Relationship

Substances

  • Amines
  • Ethers
  • Receptors, Serotonin
  • Serotonin Receptor Agonists
  • serotonin 6 receptor