Selective kappa-opioid antagonists related to naltrindole. Effect of side-chain spacer in the 5'-amidinoalkyl series

Bioorg Med Chem Lett. 2000 Oct 16;10(20):2259-61. doi: 10.1016/s0960-894x(00)00433-9.

Abstract

The study of kappa-opioid receptor function in vivo has been hampered by the limited choice of selective kappa-antagonists. Recently discovered kappa-antagonists have not yet been utilised in vivo. We here report the synthesis and in vitro evaluation of a new amidine derivative of naltrindole. It showed substantially greater kappa-selectivity in binding assays than known analogues with shorter spacer in the amidine side chain. This indicates that in nor-BNI and related selective kappa-antagonists, the second basic centre may not be ideally located.

Publication types

  • Research Support, U.S. Gov't, P.H.S.

MeSH terms

  • Amidines / chemical synthesis*
  • Amidines / chemistry
  • Amidines / pharmacology
  • Animals
  • Benzeneacetamides*
  • Binding, Competitive
  • Brain / metabolism
  • Cell Membrane / metabolism
  • Drug Design
  • Enkephalin, Ala(2)-MePhe(4)-Gly(5)- / pharmacokinetics
  • Enkephalin, D-Penicillamine (2,5)- / pharmacokinetics
  • Guinea Pigs
  • Indicators and Reagents
  • Kinetics
  • Naltrexone / analogs & derivatives*
  • Naltrexone / chemical synthesis
  • Naltrexone / chemistry
  • Naltrexone / pharmacology
  • Narcotic Antagonists / chemical synthesis*
  • Narcotic Antagonists / chemistry
  • Narcotic Antagonists / pharmacology
  • Pyrrolidines / pharmacokinetics
  • Receptors, Opioid, kappa / antagonists & inhibitors*
  • Structure-Activity Relationship

Substances

  • Amidines
  • Benzeneacetamides
  • Indicators and Reagents
  • Narcotic Antagonists
  • Pyrrolidines
  • Receptors, Opioid, kappa
  • Enkephalin, Ala(2)-MePhe(4)-Gly(5)-
  • Naltrexone
  • Enkephalin, D-Penicillamine (2,5)-
  • naltrindole
  • U 69593