Substituted 3-(4-(1,3,5-triazin-2-yl)-phenyl)-2-aminopropanoic acids as novel tryptophan hydroxylase inhibitors

Bioorg Med Chem Lett. 2009 Sep 1;19(17):5229-32. doi: 10.1016/j.bmcl.2009.07.005. Epub 2009 Jul 8.

Abstract

Tryptophan hydroxylase (TPH) is a key enzyme in the synthesis of serotonin. As a neurotransmitter, serotonin plays important physiological roles both peripherally and centrally. Here we describe the discovery of substituted triazines as a novel class of tryptophan hydroxylase inhibitors. This class of TPH inhibitors can selectively reduce serotonin levels in murine intestine after oral administration without affecting levels in the brain. These TPH inhibitors may provide novel treatments for gastrointestinal disorders associated with dysregulation of the serotonergic system, such as chemotherapy-induced emesis and irritable bowel syndrome.

MeSH terms

  • Animals
  • Binding Sites
  • Cell Line
  • Crystallography, X-Ray
  • Enzyme Inhibitors / chemical synthesis
  • Enzyme Inhibitors / chemistry*
  • Enzyme Inhibitors / pharmacology
  • Humans
  • Molecular Conformation
  • Pyrazines / chemical synthesis
  • Pyrazines / chemistry*
  • Pyrazines / pharmacology
  • Rats
  • Recombinant Proteins / antagonists & inhibitors
  • Recombinant Proteins / metabolism
  • Serotonin / biosynthesis
  • Structure-Activity Relationship
  • Tryptophan Hydroxylase / antagonists & inhibitors*
  • Tryptophan Hydroxylase / metabolism

Substances

  • Enzyme Inhibitors
  • Pyrazines
  • Recombinant Proteins
  • Serotonin
  • Tryptophan Hydroxylase