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J Med Chem. 2009 Nov 12;52(21):6926-30. doi: 10.1021/jm901074a.

14beta-Arylpropiolylamino-17-cyclopropylmethyl-7,8-dihydronormorphinones and related opioids. Further examples of pseudoirreversible mu opioid receptor antagonists.

Author information

1
School of Chemistry, University of Bristol, Bristol, U.K.

Abstract

14beta-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.

PMID:
19842669
PMCID:
PMC2788771
DOI:
10.1021/jm901074a
[Indexed for MEDLINE]
Free PMC Article

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