Synthesis and structure-activity relationships of a new series of 2α-substituted trans-4,5-dimethyl-4-(3-hydroxyphenyl)piperidine as μ-selective opioid antagonists

Bertrand Le Bourdonnec; Allan J. Goodman; Mathieu Michaut; Hai Fen Ye; Thomas M. Graczyk; Serge Belanger; Robert N. DeHaven; Roland E. Dolle

doi:10.1016/j.bmcl.2005.11.010

Synthesis and structure-activity relationships of a new series of 2α-substituted trans-4,5-dimethyl-4-(3-hydroxyphenyl)piperidine as μ-selective opioid antagonists

Bertrand Le Bourdonnec
, Allan J. Goodman
, Mathieu Michaut
, Hai Fen Ye
, Thomas M. Graczyk
, Serge Belanger
, Robert N. DeHaven
, Roland E. Dolle

Research output: Contribution to journal › Article › peer-review

3 Scopus citations

Abstract

Structure-activity relationships at the 2α-position of the piperidine ring of the trans-4,5-dimethyl-4-(3-hydroxyphenyl)piperidine μ-opioid antagonist series were investigated. This study showed that only small linear alkyl groups (methyl, propyl) are tolerated at the 2α-position of the piperidine ring of this series.

Original language	English
Pages (from-to)	864-868
Number of pages	5
Journal	Bioorganic and Medicinal Chemistry Letters
Volume	16
Issue number	4
DOIs	https://doi.org/10.1016/j.bmcl.2005.11.010
State	Published - Feb 15 2006

Keywords

Antagonist
Opioid
μ

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10.1016/j.bmcl.2005.11.010

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Le Bourdonnec, B., Goodman, A. J., Michaut, M., Ye, H. F., Graczyk, T. M., Belanger, S., DeHaven, R. N., & Dolle, R. E. (2006). Synthesis and structure-activity relationships of a new series of 2α-substituted trans-4,5-dimethyl-4-(3-hydroxyphenyl)piperidine as μ-selective opioid antagonists. Bioorganic and Medicinal Chemistry Letters, 16(4), 864-868. https://doi.org/10.1016/j.bmcl.2005.11.010

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title = "Synthesis and structure-activity relationships of a new series of 2α-substituted trans-4,5-dimethyl-4-(3-hydroxyphenyl)piperidine as μ-selective opioid antagonists",

abstract = "Structure-activity relationships at the 2α-position of the piperidine ring of the trans-4,5-dimethyl-4-(3-hydroxyphenyl)piperidine μ-opioid antagonist series were investigated. This study showed that only small linear alkyl groups (methyl, propyl) are tolerated at the 2α-position of the piperidine ring of this series.",

keywords = "Antagonist, Opioid, μ",

author = "\{Le Bourdonnec\}, Bertrand and Goodman, \{Allan J.\} and Mathieu Michaut and Ye, \{Hai Fen\} and Graczyk, \{Thomas M.\} and Serge Belanger and DeHaven, \{Robert N.\} and Dolle, \{Roland E.\}",

year = "2006",

month = feb,

day = "15",

doi = "10.1016/j.bmcl.2005.11.010",

language = "English",

volume = "16",

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journal = "Bioorganic and Medicinal Chemistry Letters",

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Le Bourdonnec, B, Goodman, AJ, Michaut, M, Ye, HF, Graczyk, TM, Belanger, S, DeHaven, RN & Dolle, RE 2006, 'Synthesis and structure-activity relationships of a new series of 2α-substituted trans-4,5-dimethyl-4-(3-hydroxyphenyl)piperidine as μ-selective opioid antagonists', Bioorganic and Medicinal Chemistry Letters, vol. 16, no. 4, pp. 864-868. https://doi.org/10.1016/j.bmcl.2005.11.010

Synthesis and structure-activity relationships of a new series of 2α-substituted trans-4,5-dimethyl-4-(3-hydroxyphenyl)piperidine as μ-selective opioid antagonists. / Le Bourdonnec, Bertrand; Goodman, Allan J.; Michaut, Mathieu et al.
In: Bioorganic and Medicinal Chemistry Letters, Vol. 16, No. 4, 15.02.2006, p. 864-868.

Research output: Contribution to journal › Article › peer-review

TY - JOUR

T1 - Synthesis and structure-activity relationships of a new series of 2α-substituted trans-4,5-dimethyl-4-(3-hydroxyphenyl)piperidine as μ-selective opioid antagonists

AU - Le Bourdonnec, Bertrand

AU - Goodman, Allan J.

AU - Michaut, Mathieu

AU - Ye, Hai Fen

AU - Graczyk, Thomas M.

AU - Belanger, Serge

AU - DeHaven, Robert N.

AU - Dolle, Roland E.

PY - 2006/2/15

Y1 - 2006/2/15

N2 - Structure-activity relationships at the 2α-position of the piperidine ring of the trans-4,5-dimethyl-4-(3-hydroxyphenyl)piperidine μ-opioid antagonist series were investigated. This study showed that only small linear alkyl groups (methyl, propyl) are tolerated at the 2α-position of the piperidine ring of this series.

AB - Structure-activity relationships at the 2α-position of the piperidine ring of the trans-4,5-dimethyl-4-(3-hydroxyphenyl)piperidine μ-opioid antagonist series were investigated. This study showed that only small linear alkyl groups (methyl, propyl) are tolerated at the 2α-position of the piperidine ring of this series.

KW - Antagonist

KW - Opioid

KW - μ

UR - https://www.scopus.com/pages/publications/30344472993

U2 - 10.1016/j.bmcl.2005.11.010

DO - 10.1016/j.bmcl.2005.11.010

M3 - Article

C2 - 16298525

AN - SCOPUS:30344472993

SN - 0960-894X

VL - 16

SP - 864

EP - 868

JO - Bioorganic and Medicinal Chemistry Letters

JF - Bioorganic and Medicinal Chemistry Letters

IS - 4

ER -

Synthesis and structure-activity relationships of a new series of 2α-substituted trans-4,5-dimethyl-4-(3-hydroxyphenyl)piperidine as μ-selective opioid antagonists

Abstract

Keywords

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