14β-Arylpropiolylamino-17-cyclopropylmethyl-7,8-dihydronormorphinones and Related Opioids. Further Examples of Pseudoirreversible μ Opioid Receptor Antagonists

Nick P R Nieland; David Rennison; Jillian H Broadbear; Lauren Purington; James H Woods; John R Traynor; John W Lewis; Stephen M Husbands

doi:10.1021/jm901074a

14β-Arylpropiolylamino-17-cyclopropylmethyl-7,8-dihydronormorphinones and Related Opioids. Further Examples of Pseudoirreversible μ Opioid Receptor Antagonists

Nick P R Nieland, David Rennison, Jillian H Broadbear, Lauren Purington, James H Woods, John R Traynor, John W Lewis, Stephen M Husbands

Department of Life Sciences

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

8 Citations (SciVal)

Abstract

14β-4’-Chlorocinnamoylaminodihydronormorphinone (2a), and analogues, are selective pseudoirreversible antagonists of the mu opioid receptor (MOR). The preparation of analogues with ethynic bonds, replacing the ethenic bond of 2a, is described. The new ligands, in mouse antinociceptive assays, had pseudoirreversible MOR antagonist activity which, in the case of 8b was of longer duration than that of 2a. The related codeinone (9b) had only antagonist activity in vivo, in contrast to 2a’s codeinone equivalent 3a, which had potent antinociceptive activity.

Original language	English
Pages (from-to)	6926-6930
Number of pages	5
Journal	Journal of Medicinal Chemistry
Volume	52
Issue number	21
DOIs	https://doi.org/10.1021/jm901074a
Publication status	Published - 2009

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Nieland, N. P. R., Rennison, D., Broadbear, J. H., Purington, L., Woods, J. H., Traynor, J. R., Lewis, J. W., & Husbands, S. M. (2009). 14β-Arylpropiolylamino-17-cyclopropylmethyl-7,8-dihydronormorphinones and Related Opioids. Further Examples of Pseudoirreversible μ Opioid Receptor Antagonists. Journal of Medicinal Chemistry, 52(21), 6926-6930. https://doi.org/10.1021/jm901074a

Nieland, NPR, Rennison, D, Broadbear, JH, Purington, L, Woods, JH, Traynor, JR, Lewis, JW & Husbands, SM 2009, '14β-Arylpropiolylamino-17-cyclopropylmethyl-7,8-dihydronormorphinones and Related Opioids. Further Examples of Pseudoirreversible μ Opioid Receptor Antagonists', Journal of Medicinal Chemistry, vol. 52, no. 21, pp. 6926-6930. https://doi.org/10.1021/jm901074a

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abstract = "14β-4{\textquoteright}-Chlorocinnamoylaminodihydronormorphinone (2a), and analogues, are selective pseudoirreversible antagonists of the mu opioid receptor (MOR). The preparation of analogues with ethynic bonds, replacing the ethenic bond of 2a, is described. The new ligands, in mouse antinociceptive assays, had pseudoirreversible MOR antagonist activity which, in the case of 8b was of longer duration than that of 2a. The related codeinone (9b) had only antagonist activity in vivo, in contrast to 2a{\textquoteright}s codeinone equivalent 3a, which had potent antinociceptive activity.",

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year = "2009",

doi = "10.1021/jm901074a",

language = "English",

volume = "52",

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T1 - 14β-Arylpropiolylamino-17-cyclopropylmethyl-7,8-dihydronormorphinones and Related Opioids. Further Examples of Pseudoirreversible μ Opioid Receptor Antagonists

AU - Nieland, Nick P R

AU - Rennison, David

AU - Broadbear, Jillian H

AU - Purington, Lauren

AU - Woods, James H

AU - Traynor, John R

AU - Lewis, John W

AU - Husbands, Stephen M

PY - 2009

Y1 - 2009

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AB - 14β-4’-Chlorocinnamoylaminodihydronormorphinone (2a), and analogues, are selective pseudoirreversible antagonists of the mu opioid receptor (MOR). The preparation of analogues with ethynic bonds, replacing the ethenic bond of 2a, is described. The new ligands, in mouse antinociceptive assays, had pseudoirreversible MOR antagonist activity which, in the case of 8b was of longer duration than that of 2a. The related codeinone (9b) had only antagonist activity in vivo, in contrast to 2a’s codeinone equivalent 3a, which had potent antinociceptive activity.

UR - https://www.scopus.com/pages/publications/71049152984

UR - http://www.ncbi.nlm.nih.gov/pmc/articles/PMC2788771/

UR - http://dx.doi.org/10.1021/jm901074a

U2 - 10.1021/jm901074a

DO - 10.1021/jm901074a

M3 - Article

SN - 0022-2623

VL - 52

SP - 6926

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JO - Journal of Medicinal Chemistry

JF - Journal of Medicinal Chemistry

IS - 21

ER -

14β-Arylpropiolylamino-17-cyclopropylmethyl-7,8-dihydronormorphinones and Related Opioids. Further Examples of Pseudoirreversible μ Opioid Receptor Antagonists

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