Structure-activity relationship studies of highly selective inhibitors of the dopamine transporter: N-benzylpiperidine analogues of 1-[2-[bis(4-fluorophenyl)methoxy]ethyl]-4-(3-phenylpropyl) piperazine

Elisabeth Greiner, Thomas Prisinzano, Edward M. Johnson, Christina M. Dersch, Jamila Marcus, John S. Partilla, Richard B. Rothman, Arthur E. Jacobson, Kenner C. Rice

Research output: Contribution to journalArticlepeer-review

20 Scopus citations

Abstract

A series of 4-[2-[bis(4-fluorophenyl)methoxy]ethyl-1-benzylpiperidines were examined for their ability to bind to the dopamine transporter (DAT), the serotonin transporter (SERT), and the norepinephrine transporter (NET). Binding results indicated that the presence of an electronwithdrawing group in the C4-position of the N-benzyl group is beneficial for binding to the DAT. Several analogues have been identified with high affinity for the DAT, up to 500-fold selectivity over the SERT and about 170-fold selectivity over the NET in binding and uptake inhibition assays.

Original languageEnglish
Pages (from-to)1465-1469
Number of pages5
JournalJournal of Medicinal Chemistry
Volume46
Issue number8
DOIs
StatePublished - Apr 10 2003

ASJC Scopus subject areas

  • Molecular Medicine
  • Drug Discovery

Fingerprint

Dive into the research topics of 'Structure-activity relationship studies of highly selective inhibitors of the dopamine transporter: N-benzylpiperidine analogues of 1-[2-[bis(4-fluorophenyl)methoxy]ethyl]-4-(3-phenylpropyl) piperazine'. Together they form a unique fingerprint.

Cite this