Potent and selective small-molecule human urotensin-II antagonists with improved pharmacokinetic profiles

Bioorg Med Chem Lett. 2008 Jul 1;18(13):3716-9. doi: 10.1016/j.bmcl.2008.05.058. Epub 2008 May 20.

Abstract

Lead compound 1 was successfully redesigned to provide compounds with improved pharmacokinetic profiles for this series of human urotensin-II antagonists. Replacement of the 2-pyrrolidinylmethyl-3-phenyl-piperidine core of 1 with a substituted N-methyl-2-(1-pyrrolidinyl)ethanamine core as in compound 7 resulted in compounds with improved oral bioavailability in rats. The relationship between stereochemistry and selectivity for hUT over the kappa-opioid receptor was also explored.

MeSH terms

  • Administration, Oral
  • Animals
  • Brain / metabolism
  • Chemistry, Pharmaceutical / methods*
  • Chromatography, High Pressure Liquid
  • Diamines / chemistry
  • Drug Design
  • Humans
  • Inhibitory Concentration 50
  • Models, Chemical
  • Rats
  • Receptors, Opioid, kappa / chemistry
  • Stereoisomerism
  • Structure-Activity Relationship
  • Urotensins / antagonists & inhibitors*
  • Urotensins / chemistry

Substances

  • Diamines
  • Receptors, Opioid, kappa
  • Urotensins
  • urotensin II