Conformationally constrained tachykinin analogues: potent and highly selective neurokinin NK-2 receptor agonists

J Med Chem. 1992 Oct 30;35(22):4195-204. doi: 10.1021/jm00100a027.

Abstract

The design and synthesis of potent and selective neurokinin NK-2 receptor agonists 12 (GR64349) and 31 are described, together with structure-activity relationships for related analogues. Compound 12 (EC50 = 3.7 nM at NK-2 receptors in the rat colon; selectivity > 1000- and > 300-fold with respect to NK-1 and NK-3 receptors, respectively) was derived by incorporation of a Gly-Leu gamma-lactam conformational constraint into the C-terminal region of the neurokinin A octapeptide analogue [Lys3]-NKA(3-10). Compound 31 (EC50 = 15 nM in rat colon) contains a novel fused-bicyclic constraint at the corresponding site in the substance P hexapeptide analogue [Ava6]-SP(6-11).

MeSH terms

  • Amino Acid Sequence
  • Animals
  • Guinea Pigs
  • In Vitro Techniques
  • Lactams / chemical synthesis
  • Lactams / pharmacology
  • Male
  • Models, Molecular
  • Molecular Sequence Data
  • Muscle Contraction / drug effects
  • Muscle, Smooth / drug effects
  • Protein Conformation
  • Rats
  • Receptors, Neurotransmitter / drug effects*
  • Receptors, Tachykinin
  • Stereoisomerism
  • Structure-Activity Relationship
  • Tachykinins / chemical synthesis*
  • Tachykinins / pharmacology

Substances

  • Lactams
  • Receptors, Neurotransmitter
  • Receptors, Tachykinin
  • Tachykinins