Synthesis, dopamine and serotonin transporter binding affinities of novel analogues of meperidine

Stacey A. Lomenzo, Sari E Izenwasser, Robert M. Gerdes, Jonathan L. Katz, Theresa Kopajtic, Mark L. Trudell

Research output: Contribution to journalArticle

11 Citations (Scopus)

Abstract

A series of meperidine analogues was synthesized and the binding affinities for the dopamine and serotonin transporters were determined. The substituents on the phenyl ring greatly influenced the potency and selectivity of these compounds for the transporter binding sites. In general, meperidine (3) and its analogues were more selective for serotonin transporter binding sites and the esters 9 were more potent than the corresponding nitriles 8. The 3,4-dichloro derivative 9e was the most potent ligand of the series for dopamine transporter binding sites while the 2- naphthyl derivative 9g exhibited the most potent binding affinity and was highly selective for serotonin transporter binding sites.

Original languageEnglish
Pages (from-to)3273-3276
Number of pages4
JournalBioorganic and Medicinal Chemistry Letters
Volume9
Issue number23
StatePublished - Dec 6 1999

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Serotonin Plasma Membrane Transport Proteins
Meperidine
Dopamine Plasma Membrane Transport Proteins
Binding Sites
Derivatives
Nitriles
Esters
Ligands

ASJC Scopus subject areas

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

Cite this

Synthesis, dopamine and serotonin transporter binding affinities of novel analogues of meperidine. / Lomenzo, Stacey A.; Izenwasser, Sari E; Gerdes, Robert M.; Katz, Jonathan L.; Kopajtic, Theresa; Trudell, Mark L.

In: Bioorganic and Medicinal Chemistry Letters, Vol. 9, No. 23, 06.12.1999, p. 3273-3276.

Research output: Contribution to journalArticle

Lomenzo, Stacey A. ; Izenwasser, Sari E ; Gerdes, Robert M. ; Katz, Jonathan L. ; Kopajtic, Theresa ; Trudell, Mark L. / Synthesis, dopamine and serotonin transporter binding affinities of novel analogues of meperidine. In: Bioorganic and Medicinal Chemistry Letters. 1999 ; Vol. 9, No. 23. pp. 3273-3276.
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