8-Aminocyclazocine analogues: synthesis and structure-activity relationships

Bioorg Med Chem Lett. 2000 Jan 17;10(2):183-7. doi: 10.1016/s0960-894x(99)00670-8.

Abstract

Opioid binding affinities were assessed for a series of cyclazocine analogues where the prototypic 8-OH substituent of cyclazocine was replaced by amino and substituted-amino groups. For mu and kappa opioid receptors, secondary amine derivatives having the (2R,6R,11R)-configuration had the highest affinity. Most targets were efficiently synthesized from the triflate of cyclazocine or its enantiomers using Pd-catalyzed amination procedures.

Publication types

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

MeSH terms

  • Analgesics / chemical synthesis*
  • Analgesics / pharmacology
  • Animals
  • Benzeneacetamides*
  • Binding, Competitive
  • Brain / drug effects
  • Cyclazocine / analogs & derivatives*
  • Cyclazocine / chemistry
  • Enkephalin, Ala(2)-MePhe(4)-Gly(5)- / metabolism
  • Guinea Pigs
  • Molecular Structure
  • Naltrexone / analogs & derivatives
  • Naltrexone / metabolism
  • Narcotic Antagonists
  • Pyrrolidines / metabolism
  • Receptors, Opioid / agonists
  • Stereoisomerism
  • Structure-Activity Relationship

Substances

  • 8-aminocyclazocine
  • Analgesics
  • Benzeneacetamides
  • Narcotic Antagonists
  • Pyrrolidines
  • Receptors, Opioid
  • Enkephalin, Ala(2)-MePhe(4)-Gly(5)-
  • Naltrexone
  • naltrindole
  • U 69593
  • Cyclazocine