Synthesis and SAR of 1-alkyl-2-phenylethylamine derivatives designed from N,N-dipropyl-4-methoxy-3-(2-phenylethoxy)phenylethylamine to discover sigma(1) ligands

J Med Chem. 1999 Sep 23;42(19):3965-70. doi: 10.1021/jm990135j.

Abstract

The synthesis and structure-activity relationships (SAR) of 1-alkyl-2-phenylethylamine derivatives 5-8 designed from N, N-dipropyl-2-[4-methoxy-3-(2-phenylethoxy)phenyl]ethylamine hydrochloride (1, NE-100) are presented. The SAR between compound 1 and 1-alkyl-2-phenylethylamine derivatives suggested that the alkyl group on the 1-position carbon of 2-[4-methoxy-3-(2-phenylethyl)phenyl]ethylamine derivatives played the role of one of the propyl groups on the aminic nitrogen of compound 1. (-)-N-Propyl-1-butyl-2-[4-methoxy-3-(2-phenylethoxy)phenyl]ethylam ine hydrochloride ((-)-6d, NE-537) and (-)-N-propyl-1-(3-methybutyl)-2-[4-methoxy-3-(2-phenylethoxy )phenyl]e thylamine hydrochloride ((-)-6i, NE-535), typical compounds in this series, have potent and selective sigma(1) affinity.

MeSH terms

  • Alkylation
  • Anisoles / chemistry*
  • Anisoles / pharmacology*
  • Antipsychotic Agents / chemistry*
  • Antipsychotic Agents / pharmacology*
  • Isomerism
  • Ligands
  • Phenethylamines
  • Propylamines / chemistry*
  • Propylamines / pharmacology*
  • Structure-Activity Relationship

Substances

  • Anisoles
  • Antipsychotic Agents
  • Ligands
  • Phenethylamines
  • Propylamines
  • N,N-dipropyl-2-(4-methoxy-3-(2-phenylethoxy)phenyl)ethylamine monohydrochloride