Naphtho and benzo analogues of the kappa opioid agonist trans-(+/-)-3,4-dichloro-N-methyl-N-[2-(1-pyrrolidinyl)cyclohexyl] benzeneacetamide

J P Freeman; E T Michalson; S V D'Andrea; L Baczynskyj; P F Von Voigtlander; R A Lahti; M W Smith; C F Lawson; T A Scahill; S A Mizsak

doi:10.1021/jm00110a021

Naphtho and benzo analogues of the kappa opioid agonist trans-(+/-)-3,4-dichloro-N-methyl-N-[2-(1-pyrrolidinyl)cyclohexyl] benzeneacetamide

J Med Chem. 1991 Jun;34(6):1891-6. doi: 10.1021/jm00110a021.

Authors

J P Freeman¹, E T Michalson, S V D'Andrea, L Baczynskyj, P F Von Voigtlander, R A Lahti, M W Smith, C F Lawson, T A Scahill, S A Mizsak, et al.

Affiliation

¹ Department of Chemistry and Biochemistry, University of Notre Dame, Indiana 46556.

PMID: 1648141
DOI: 10.1021/jm00110a021

Abstract

Further elaboration on the structure-activity relationships in our U-50,488 series has revealed that benzologation of this cyclohexane-1,2-diamine derivative provides compounds which either maintain the interaction with the kappa receptor (e.g. compounds 3a and 5a in the phenylacetamido series) or eliminate the mu receptor mediated analgesia (e.g. compounds 3-6 in the benzamido series). Naphthologation also caused the elimination of mu receptor mediated analgesia (e.g. compounds 17a and 17b).

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

3,4-Dichloro-N-methyl-N-(2-(1-pyrrolidinyl)-cyclohexyl)-benzeneacetamide, (trans)-Isomer
Analgesics*
Animals
Magnetic Resonance Spectroscopy
Mice
Narcotic Antagonists*
Pyrrolidines / chemistry
Pyrrolidines / pharmacology*
Receptors, Opioid, kappa
Structure-Activity Relationship

Substances

Analgesics
Narcotic Antagonists
Pyrrolidines
Receptors, Opioid, kappa
3,4-Dichloro-N-methyl-N-(2-(1-pyrrolidinyl)-cyclohexyl)-benzeneacetamide, (trans)-Isomer