Synthesis and structure-activity studies of benzyl ester meperidine and normeperidine derivatives as selective serotonin transporter ligands

Xiaobo Gu, Sari Izenwasser, Dean Wade, Amy Housman, Gerard Gulasey, Jill B. Rhoden, Christopher D. Savoie, David L. Mobley, Stacey A. Lomenzo, Mark L. Trudell

Research output: Contribution to journalArticle

3 Scopus citations

Abstract

A series of benzyl esters of meperidine and normeperidine were synthesized and evaluated for binding affinity at serotonin, dopamine and norepinephrine transporters. The 4-methoxybenzyl ester 8b and 4-nitrobenzyl ester 8c in the meperidine series and 4-methoxybenzyl ester 14a in the normeperidine series exhibited low nanomolar binding affinities at the SERT (Ki values <2 nM) and high SERT selectivity (DAT/SERT >1500 and NET/SERT >1500).

Original languageEnglish (US)
Pages (from-to)8356-8364
Number of pages9
JournalBioorganic and Medicinal Chemistry
Volume18
Issue number23
DOIs
StatePublished - Dec 1 2010

Keywords

  • Depression
  • Dopamine transporters
  • Meperidine
  • Norepinephrine transporters
  • Normeperidine
  • Serotonin transporter

ASJC Scopus subject areas

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

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