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

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

Psychiatry & Behavioral Sciences

Research output: Contribution to journal › Article

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

Original language	English (US)
Pages (from-to)	8356-8364
Number of pages	9
Journal	Bioorganic and Medicinal Chemistry
Volume	18
Issue number	23
DOIs	https://doi.org/10.1016/j.bmc.2010.09.060
State	Published - Dec 1 2010

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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

Cite this

Gu, X., Izenwasser, S., Wade, D., Housman, A., Gulasey, G., Rhoden, J. B., Savoie, C. D., Mobley, D. L., Lomenzo, S. A., & Trudell, M. L. (2010). Synthesis and structure-activity studies of benzyl ester meperidine and normeperidine derivatives as selective serotonin transporter ligands. Bioorganic and Medicinal Chemistry, 18(23), 8356-8364. https://doi.org/10.1016/j.bmc.2010.09.060

Synthesis and structure-activity studies of benzyl ester meperidine and normeperidine derivatives as selective serotonin transporter ligands. / Gu, Xiaobo; Izenwasser, Sari; Wade, Dean; Housman, Amy; Gulasey, Gerard; Rhoden, Jill B.; Savoie, Christopher D.; Mobley, David L.; Lomenzo, Stacey A.; Trudell, Mark L.

In: Bioorganic and Medicinal Chemistry, Vol. 18, No. 23, 01.12.2010, p. 8356-8364.

Research output: Contribution to journal › Article

Gu, X, Izenwasser, S, Wade, D, Housman, A, Gulasey, G, Rhoden, JB, Savoie, CD, Mobley, DL, Lomenzo, SA & Trudell, ML 2010, 'Synthesis and structure-activity studies of benzyl ester meperidine and normeperidine derivatives as selective serotonin transporter ligands', Bioorganic and Medicinal Chemistry, vol. 18, no. 23, pp. 8356-8364. https://doi.org/10.1016/j.bmc.2010.09.060

Gu, Xiaobo ; Izenwasser, Sari ; Wade, Dean ; Housman, Amy ; Gulasey, Gerard ; Rhoden, Jill B. ; Savoie, Christopher D. ; Mobley, David L. ; Lomenzo, Stacey A. ; Trudell, Mark L. / Synthesis and structure-activity studies of benzyl ester meperidine and normeperidine derivatives as selective serotonin transporter ligands. In: Bioorganic and Medicinal Chemistry. 2010 ; Vol. 18, No. 23. pp. 8356-8364.

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10.1016/j.bmc.2010.09.060