Synthesis and dopamine transporter affinity of chiral 1-[2-[bis(4-fluorophenyl)methoxy]ethyl]-4-(2-hydroxypropyl)piperazines as potential cocaine abuse therapeutic agents

Ling Wei Hsin, Thomas Prisinzano, Chavon R. Wilkerson, Christina M. Dersch, Robert Horel, Arthur E. Jacobson, Richard B. Rothman, Kenner C. Rice

Research output: Contribution to journalArticlepeer-review

16 Scopus citations

Abstract

A series of optically pure phenyl-and non-phenyl-substituted 1-[2-[bis(4-fluorophenyl)methoxy]ethyl]-4-(2-hydroxypropyl)piperazines was synthesized and their binding affinity for dopamine transporter (DAT) was investigated. The analogues with a hydroxyl group in the S configuration were more selective for the DAT over the serotonin transporter (SERT) than the corresponding R enantiomers. Compound (+)-11 showed high affinity and selectivity for DAT over the SERT and, therefore, is a potential candidate for the development of a long-acting cocaine abuse therapeutic agent.

Original languageEnglish
Pages (from-to)553-556
Number of pages4
JournalBioorganic and Medicinal Chemistry Letters
Volume13
Issue number3
DOIs
StatePublished - Feb 2003

Bibliographical note

Funding Information:
The authors (L.M.C., N.I.D.D.K.) thank the National Institute on Drug Abuse, NIH, for partial financial support of our research program. The authors also thank Noel Whitaker and Wesley White (N.I.D.D.K., N.I.H.) for mass spectral analysis.

ASJC Scopus subject areas

  • Biochemistry
  • Molecular Medicine
  • Molecular Biology
  • Pharmaceutical Science
  • Drug Discovery
  • Clinical Biochemistry
  • Organic Chemistry

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