Rational design of high affinity tachykinin NK1 receptor antagonists

Bioorg Med Chem. 1994 May;2(5):357-70. doi: 10.1016/s0968-0896(00)82192-6.

Abstract

The rational design of a non-peptide tachykinin NK1 receptor antagonist, [(2-benzofuran)-CH2OCO]-(R)-alpha-MeTrp-(S)-NHCH(CH3)P h (28, PD 154075) is described. Compound 28 has a Ki = 9 and 0.35 nM for the NK1 receptor binding site in guinea-pig cerebral cortex membranes and human IM9, cells respectively (using [125I] Bolton-Hunter-SP as the radioligand). It is a potent antagonist in vitro where it antagonises the contractions mediated by SPOMe in the guinea-pig ileum (KB = 0.3 nM). Compound 28 is active in vivo in the guinea-pig plasma extravasation model, where it is able to block the SPOMe-induced protein plasma extravasation (monitored by Evans Blue) in the bladder with an ID50 of 0.02 mg kg-1 iv.

MeSH terms

  • Animals
  • Blood Proteins / metabolism
  • Cell Line
  • Cerebral Cortex / drug effects
  • Cerebral Cortex / metabolism
  • Drug Design
  • Guinea Pigs
  • Humans
  • Ileum / drug effects
  • In Vitro Techniques
  • Kinetics
  • Magnetic Resonance Spectroscopy
  • Male
  • Molecular Structure
  • Neurokinin-1 Receptor Antagonists*
  • Tryptophan / analogs & derivatives*
  • Tryptophan / chemical synthesis
  • Tryptophan / chemistry
  • Tryptophan / pharmacology
  • Urinary Bladder / drug effects

Substances

  • Blood Proteins
  • Neurokinin-1 Receptor Antagonists
  • Tryptophan
  • PD 154075