TY - JOUR
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
N2 - 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.
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 - http://www.scopus.com/inward/record.url?scp=71049152984&partnerID=8YFLogxK
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
EP - 6930
JO - Journal of Medicinal Chemistry
JF - Journal of Medicinal Chemistry
IS - 21
ER -