Tranylcypromine substituted cis-hydroxycyclobutylnaphthamides as potent and selective dopamine D₃ receptor antagonists

J Med Chem. 2014 Jun 12;57(11):4962-8. doi: 10.1021/jm401798r. Epub 2014 Jun 3.

Abstract

We report a class of potent and selective dopamine D3 receptor antagonists based upon tranylcypromine. Although tranylcypromine has a low affinity for the rat D3 receptor (K(i) = 12.8 μM), our efforts have yielded (1R,2S)-11 (CJ-1882), which has K(i) values of 2.7 and 2.8 nM at the rat and human dopamine D3 receptors, respectively, and displays respective selectivities of >10000-fold and 223-fold over the rat and human D2 receptors. Evaluation in a β-arrestin functional assay showed that (1R,2S)-11 is a potent and competitive antagonist at the human D3 receptor.

Publication types

  • Research Support, N.I.H., Extramural
  • Research Support, N.I.H., Intramural

MeSH terms

  • Animals
  • Arrestins / metabolism
  • Cell Line
  • Cyclobutanes / chemistry*
  • Cyclobutanes / pharmacology
  • Humans
  • Male
  • Naphthalenes / chemistry*
  • Naphthalenes / pharmacology
  • Radioligand Assay
  • Rats, Sprague-Dawley
  • Receptors, Dopamine D3 / antagonists & inhibitors*
  • Stereoisomerism
  • Structure-Activity Relationship
  • Tranylcypromine / analogs & derivatives*
  • Tranylcypromine / chemistry*
  • Tranylcypromine / pharmacology
  • beta-Arrestins

Substances

  • Arrestins
  • Cyclobutanes
  • N-(3-(2-((2-(4-chlorophenyl)cyclopropyl)(propyl)-amino)ethyl)-3-hydroxycyclobutyl)-2-naphthamide
  • Naphthalenes
  • Receptors, Dopamine D3
  • beta-Arrestins
  • Tranylcypromine