Discovery of a novel class of selective non-peptide antagonists for the human neurokinin-3 receptor. 1. Identification of the 4-quinolinecarboxamide framework

J Med Chem. 1997 Jun 6;40(12):1794-807. doi: 10.1021/jm960818o.

Abstract

A novel class of potent and selective non-peptide neurokinin-3 (NK-3) receptor antagonists, featuring the 4-quinolinecarboxamide framework, has been designed based upon chemically diverse NK-1 receptor antagonists. The novel compounds 33-76, prompted by chemical modifications of the prototype 4, have been characterized by binding analysis using a membrane preparation of chinese hamster ovary (CHO) cells expressing the human neurokinin-3 receptors (hNK-3-CHO), and clear structure-activity relationships (SARs) have been established. From SARs, (R)-N-[alpha-(methoxycarbonyl)benzyl]-2-phenylquinoline-4-carboxamide (65, SB 218795, hNK-3-CHO binding Ki = 13 nM) emerged as one of the most potent compounds of this novel class. Selectivity studies versus the other neurokinin receptors (hNK-2-CHO and hNK-1-CHO) revealed that 65 is about 90-fold selective for hNK-3 versus hNK-2 receptors (hNK-2-CHO binding Ki = 1221 nM) and over 7000-fold selective versus hNK-1 receptors (hNK-1-CHO binding Ki = > 100 microM). In vitro functional studies in rabbit isolated iris sphincter muscle preparation demonstrated that 65 is a competitive antagonist of the contractile response induced by the potent and selective NK-3 receptor agonist senktide with a Kb = 43 nM. Overall, the data indicate that 65 is a potent and selective hNK-3 receptor antagonist and a useful lead for further chemical optimization.

MeSH terms

  • Animals
  • Binding, Competitive
  • CHO Cells
  • Chemical Phenomena
  • Chemistry, Physical
  • Cricetinae
  • Humans
  • Hydrogen Bonding
  • Molecular Structure
  • Muscle Contraction / drug effects
  • Peptide Fragments / pharmacology
  • Quinolines / chemical synthesis*
  • Quinolines / metabolism
  • Rabbits
  • Receptors, Neurokinin-3 / antagonists & inhibitors*
  • Receptors, Neurokinin-3 / genetics
  • Receptors, Neurokinin-3 / metabolism
  • Recombinant Proteins / metabolism
  • Stereoisomerism
  • Structure-Activity Relationship
  • Substance P / analogs & derivatives
  • Substance P / pharmacology

Substances

  • Peptide Fragments
  • Quinolines
  • Receptors, Neurokinin-3
  • Recombinant Proteins
  • SB 218795
  • senktide
  • Substance P