Discovery of spirocyclic proline tryptophan hydroxylase-1 inhibitors

Bioorg Med Chem Lett. 2016 Feb 15;26(4):1124-9. doi: 10.1016/j.bmcl.2016.01.064. Epub 2016 Jan 22.

Abstract

The central role of the biogenic monoamine serotonin (5-hydroxytryptamine, 5-HT) as a neurotransmitter with important cognitive and behavioral functions is well known. However, 5-HT produced in the brain only accounts for approximately 5% of the total amount of 5-HT generated in the body. At the onset of our work, it appeared that substituted phenylalanine derivatives or related aryl amino acids were required to produce potent inhibitors of TPH1, as significant losses of inhibitory activity were noted in the absence of this structural element. We disclose herein the discovery of a new class of TPH1 inhibitors that significantly lower peripherally 5-HT.

Keywords: 5-HT; Peripheral serotonin; Spirocycle; TPH1.

MeSH terms

  • Animals
  • Binding Sites
  • Brain / metabolism
  • Drug Design
  • Half-Life
  • Humans
  • Inhibitory Concentration 50
  • Molecular Docking Simulation
  • Proline / analogs & derivatives*
  • Proline / chemical synthesis
  • Proline / pharmacokinetics
  • Protein Binding
  • Protein Structure, Tertiary
  • Rats
  • Serotonin / metabolism
  • Spiro Compounds / chemistry
  • Structure-Activity Relationship
  • Tryptophan Hydroxylase / antagonists & inhibitors*
  • Tryptophan Hydroxylase / metabolism

Substances

  • Spiro Compounds
  • Serotonin
  • Proline
  • TPH1 protein, human
  • Tryptophan Hydroxylase