Discovery of a novel class of substituted pyrrolooctahydroisoquinolines as potent and selective delta opioid agonists, based on an extension of the message-address concept

J Med Chem. 1997 Sep 26;40(20):3192-8. doi: 10.1021/jm9608218.

Abstract

This paper describes the design and synthesis of compounds belonging to a novel class of substituted pyrrolooctahydroisoquinolines which are potent and selective delta opioid agonists. Molecular modeling studies performed on known, selective delta ligands such as (+)-3 and the potent delta agonists SNC 80 led to the identification of the carboxamido moiety of the latter as a putative nonaromatic delta address. Insertion of this moiety onto the octahydroisoquinoline opioid message resulted in (+/-)-5b, a potent and selective delta ligand. The active enantiomer, (-)-5b, displayed nanomolar affinity for the delta receptor (Ki = 0.9 nM) with good mu/delta and kappa/delta binding selectivity ratios (140 and 1480, respectively). In addition, (-)-5b behaved as a full delta agonist in the mouse vas deferens bioassay having an IC50 = 25 nM and being antagonised in the presence of 30 nM naltrindole (NTI). These studies, based on the message-address concept, indicated that the nonaromatic (N,N-diethylamino)carbonyl moiety is a viable alternative to the classical benzene ring as a delta opioid address. Preliminary in vivo studies showed that (+/-)-5b produced a dose-related antinociception in the mouse abdominal constriction test after intracerebroventricular administration (ED50 = 1.6 micrograms/mouse).

MeSH terms

  • Animals
  • Benzamides / chemistry
  • Benzamides / pharmacology
  • Brain / drug effects
  • Brain / metabolism
  • Computer Simulation
  • Dose-Response Relationship, Drug
  • Drug Design
  • Enkephalin, Leucine-2-Alanine / metabolism
  • Indoles / chemistry*
  • Indoles / pharmacology
  • Isoquinolines / chemistry*
  • Isoquinolines / pharmacology
  • Ligands
  • Male
  • Mice
  • Models, Molecular
  • Naltrexone / analogs & derivatives
  • Naltrexone / pharmacology
  • Narcotic Antagonists / pharmacology
  • Nociceptors / drug effects
  • Piperazines / chemistry
  • Piperazines / pharmacology
  • Pyrroles / chemistry*
  • Pyrroles / pharmacology
  • Quinolines / chemistry
  • Quinolines / metabolism
  • Receptors, Opioid, delta / agonists*
  • Signal Transduction
  • Stereoisomerism
  • Vas Deferens / drug effects

Substances

  • 2-((diethylamino)carbonyl)-6-ethyl-8a-(3-hydroxyphenyl)-3-methyl-4,4a,5,6,7,8,8a,9-octahydro-1H-pyrrolo(2,3-g)isoquinoline
  • Benzamides
  • Indoles
  • Isoquinolines
  • Ligands
  • Narcotic Antagonists
  • Piperazines
  • Pyrroles
  • Quinolines
  • Receptors, Opioid, delta
  • TAN 67
  • 4-(alpha-(4-allyl-2,5-dimethyl-1-piperazinyl)-3-methoxybenzyl)-N,N-diethylbenzamide
  • Naltrexone
  • Enkephalin, Leucine-2-Alanine
  • naltrindole