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

doi:10.1016/j.bmc.2010.09.060

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

Journal article

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Peer reviewed

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 and Mark L Trudell

Bioorganic & medicinal chemistry, Vol.18(23), pp.8356-8364

2010-12-01

DOI: https://doi.org/10.1016/j.bmc.2010.09.060

PMCID: PMC3713777

PMID: 20980153

Abstract

Depression

Serotonin transporter

Norepinephrine transporters

Normeperidine

Dopamine transporters

Meperidine

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 <2nM) and high SERT selectivity (DAT/SERT >1500 and NET/SERT >1500).

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Collaboration types: Domestic collaboration
Citation topics: 1 Clinical & Life Sciences; 1.5 Neuroscience; 1.5.338 Serotonin
Web Of Science research areas: Biochemistry & Molecular Biology; Chemistry, Medicinal; Chemistry, Organic
ESI research areas: Chemistry

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Details

Title: Synthesis and structure–activity studies of benzyl ester meperidine and normeperidine derivatives as selective serotonin transporter ligands
Creators: Xiaobo Gu - Department of Chemistry, University of New Orleans, New Orleans, LA 70148, USA
Sari Izenwasser - Department of Psychiatry and Behavioral Sciences, University of Miami Miller School of Medicine, Miami, FL 33136, USA
Dean Wade - Department of Psychiatry and Behavioral Sciences, University of Miami Miller School of Medicine, Miami, FL 33136, USA
Amy Housman - Department of Psychiatry and Behavioral Sciences, University of Miami Miller School of Medicine, Miami, FL 33136, USA
Gerard Gulasey - Department of Psychiatry and Behavioral Sciences, University of Miami Miller School of Medicine, Miami, FL 33136, USA
Jill B Rhoden - Department of Chemistry, University of New Orleans, New Orleans, LA 70148, USA
Christopher D Savoie - Department of Chemistry, University of New Orleans, New Orleans, LA 70148, USA
David L Mobley - Department of Chemistry, University of New Orleans, New Orleans, LA 70148, USA
Stacey A Lomenzo - Department of Chemistry, University of New Orleans, New Orleans, LA 70148, USA
Mark L Trudell - Department of Chemistry, University of New Orleans, New Orleans, LA 70148, USA
Publication Details: Bioorganic & medicinal chemistry, Vol.18(23), pp.8356-8364
Publisher: Elsevier Ltd
Academic Unit: Miller School of Medicine; UMMG Dept of Psychiatry & Behavioral Sciences
Language: English
Resource Type: Journal article
PMID: 20980153
PMCID: PMC3713777
Record Identifier: 991031561492902976