Novel trans-3,4-dimethyl-4-(3-hydroxyphenyl)piperidines as μ opioid receptor antagonists with improved opioid receptor selectivity profiles

Bertrand Le Bourdonnec; William M. Barker; Serge Belanger; Daniel D. Wiant; Nathalie C. Conway-James; Joel A. Cassel; Timothy J. O'Neill; Patrick J. Little; Robert N. DeHaven; Diane L. DeHaven-Hudkins; Roland E. Dolle

doi:10.1016/j.bmcl.2008.01.106

Novel trans-3,4-dimethyl-4-(3-hydroxyphenyl)piperidines as μ opioid receptor antagonists with improved opioid receptor selectivity profiles

Bertrand Le Bourdonnec
, William M. Barker
, Serge Belanger
, Daniel D. Wiant
, Nathalie C. Conway-James
, Joel A. Cassel
, Timothy J. O'Neill
, Patrick J. Little
, Robert N. DeHaven
, Diane L. DeHaven-Hudkins
, Roland E. Dolle

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

5 Scopus citations

Abstract

A series of N-substituted trans-3,4-dimethyl-4-(3-hydroxyphenyl)piperidines, μ opioid receptor antagonists, analogs of alvimopan, were prepared using solid phase methodology. This study led to the identification of a highly selective μ opioid receptor antagonist, which interacts selectively with μ peripheral receptors.

Original language	English
Pages (from-to)	2006-2012
Number of pages	7
Journal	Bioorganic and Medicinal Chemistry Letters
Volume	18
Issue number	6
DOIs	https://doi.org/10.1016/j.bmcl.2008.01.106
State	Published - Mar 15 2008

Keywords

Opioid
Solid phase synthesis
μ receptors

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10.1016/j.bmcl.2008.01.106

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Le Bourdonnec, B., Barker, W. M., Belanger, S., Wiant, D. D., Conway-James, N. C., Cassel, J. A., O'Neill, T. J., Little, P. J., DeHaven, R. N., DeHaven-Hudkins, D. L., & Dolle, R. E. (2008). Novel trans-3,4-dimethyl-4-(3-hydroxyphenyl)piperidines as μ opioid receptor antagonists with improved opioid receptor selectivity profiles. Bioorganic and Medicinal Chemistry Letters, 18(6), 2006-2012. https://doi.org/10.1016/j.bmcl.2008.01.106

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title = "Novel trans-3,4-dimethyl-4-(3-hydroxyphenyl)piperidines as μ opioid receptor antagonists with improved opioid receptor selectivity profiles",

abstract = "A series of N-substituted trans-3,4-dimethyl-4-(3-hydroxyphenyl)piperidines, μ opioid receptor antagonists, analogs of alvimopan, were prepared using solid phase methodology. This study led to the identification of a highly selective μ opioid receptor antagonist, which interacts selectively with μ peripheral receptors.",

keywords = "Opioid, Solid phase synthesis, μ receptors",

author = "\{Le Bourdonnec\}, Bertrand and Barker, \{William M.\} and Serge Belanger and Wiant, \{Daniel D.\} and Conway-James, \{Nathalie C.\} and Cassel, \{Joel A.\} and O'Neill, \{Timothy J.\} and Little, \{Patrick J.\} and DeHaven, \{Robert N.\} and DeHaven-Hudkins, \{Diane L.\} and Dolle, \{Roland E.\}",

year = "2008",

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day = "15",

doi = "10.1016/j.bmcl.2008.01.106",

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Le Bourdonnec, B, Barker, WM, Belanger, S, Wiant, DD, Conway-James, NC, Cassel, JA, O'Neill, TJ, Little, PJ, DeHaven, RN, DeHaven-Hudkins, DL & Dolle, RE 2008, 'Novel trans-3,4-dimethyl-4-(3-hydroxyphenyl)piperidines as μ opioid receptor antagonists with improved opioid receptor selectivity profiles', Bioorganic and Medicinal Chemistry Letters, vol. 18, no. 6, pp. 2006-2012. https://doi.org/10.1016/j.bmcl.2008.01.106

TY - JOUR

T1 - Novel trans-3,4-dimethyl-4-(3-hydroxyphenyl)piperidines as μ opioid receptor antagonists with improved opioid receptor selectivity profiles

AU - Le Bourdonnec, Bertrand

AU - Barker, William M.

AU - Belanger, Serge

AU - Wiant, Daniel D.

AU - Conway-James, Nathalie C.

AU - Cassel, Joel A.

AU - O'Neill, Timothy J.

AU - Little, Patrick J.

AU - DeHaven, Robert N.

AU - DeHaven-Hudkins, Diane L.

AU - Dolle, Roland E.

PY - 2008/3/15

Y1 - 2008/3/15

N2 - A series of N-substituted trans-3,4-dimethyl-4-(3-hydroxyphenyl)piperidines, μ opioid receptor antagonists, analogs of alvimopan, were prepared using solid phase methodology. This study led to the identification of a highly selective μ opioid receptor antagonist, which interacts selectively with μ peripheral receptors.

AB - A series of N-substituted trans-3,4-dimethyl-4-(3-hydroxyphenyl)piperidines, μ opioid receptor antagonists, analogs of alvimopan, were prepared using solid phase methodology. This study led to the identification of a highly selective μ opioid receptor antagonist, which interacts selectively with μ peripheral receptors.

KW - Opioid

KW - Solid phase synthesis

KW - μ receptors

UR - https://www.scopus.com/pages/publications/40749139396

U2 - 10.1016/j.bmcl.2008.01.106

DO - 10.1016/j.bmcl.2008.01.106

M3 - Article

C2 - 18313920

AN - SCOPUS:40749139396

SN - 0960-894X

VL - 18

SP - 2006

EP - 2012

JO - Bioorganic and Medicinal Chemistry Letters

JF - Bioorganic and Medicinal Chemistry Letters

IS - 6

ER -

Novel trans-3,4-dimethyl-4-(3-hydroxyphenyl)piperidines as μ opioid receptor antagonists with improved opioid receptor selectivity profiles

Abstract

Keywords

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