Synthesis and Structure−Activity Relationships of 3,8-Diazabicyclo[4.2.0]octane Ligands, Potent Nicotinic Acetylcholine Receptor Agonists
Jennifer M Frost (née Pac
1
,
William H. Bunnelle
1
,
Karin R Tietje
1
,
David C Anderson
1
,
Lynne E Rueter
1
,
Peter Curzon
1
,
Carol S. Surowy
1
,
Jianquo Ji
1
,
Jerome F. Daanen
1
,
Kathy L Kohlhaas
1
,
Michael J. Buckley
1
,
Rodger F Henry
1
,
Tino Dyhring
1
,
P. Ahring
1
,
Michael Meyer
1
1
Neuroscience Research, Abbott Laboratories, Abbott Park, Illinois 60064, and NeuroSearch A/S, 93 Pederstrupvej, DK-2750 Ballerup, Denmark
|
Publication type: Journal Article
Publication date: 2006-12-01
scimago Q1
wos Q1
SJR: 1.801
CiteScore: 11.5
Impact factor: 6.8
ISSN: 00222623, 15204804
PubMed ID:
17181167
Drug Discovery
Molecular Medicine
Abstract
A series of potent neuronal nicotinic acetylcholine receptor (nAChR) ligands based on a 3,8-diazabicyclo[4.2.0]octane core have been synthesized and evaluated for affinity and agonist efficacy at the human high affinity nicotine recognition site (halpha4beta2) and in a rat model of persistent nociceptive pain (formalin model). Numerous analogs in this series exhibit picomolar affinity in radioligand binding assays and nanomolar agonist potency in functional assays, placing them among the most potent nAChR ligands known for the halpha4beta2 receptor. Several of the compounds reported in this study (i.e., 24, 25, 28, 30, 32, and 47) exhibit equivalent or greater affinity for the halpha4beta2 receptor relative to epibatidine, and like epibatidine, many exhibit robust analgesic efficacy in the rat formalin model of persistent pain.
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Frost (née Pac J. M. et al. Synthesis and Structure−Activity Relationships of 3,8-Diazabicyclo[4.2.0]octane Ligands, Potent Nicotinic Acetylcholine Receptor Agonists // Journal of Medicinal Chemistry. 2006. Vol. 49. No. 26. pp. 7843-7853.
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Frost (née Pac J. M., Bunnelle W. H., Tietje K. R., Anderson D. C., Rueter L. E., Curzon P., Surowy C. S., Ji J., Daanen J. F., Kohlhaas K. L., Buckley M. J., Henry R. F., Dyhring T., Ahring P., Meyer M. Synthesis and Structure−Activity Relationships of 3,8-Diazabicyclo[4.2.0]octane Ligands, Potent Nicotinic Acetylcholine Receptor Agonists // Journal of Medicinal Chemistry. 2006. Vol. 49. No. 26. pp. 7843-7853.
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RIS
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TY - JOUR
DO - 10.1021/jm060846z
UR - https://doi.org/10.1021/jm060846z
TI - Synthesis and Structure−Activity Relationships of 3,8-Diazabicyclo[4.2.0]octane Ligands, Potent Nicotinic Acetylcholine Receptor Agonists
T2 - Journal of Medicinal Chemistry
AU - Frost (née Pac, Jennifer M
AU - Bunnelle, William H.
AU - Tietje, Karin R
AU - Anderson, David C
AU - Rueter, Lynne E
AU - Curzon, Peter
AU - Surowy, Carol S.
AU - Ji, Jianquo
AU - Daanen, Jerome F.
AU - Kohlhaas, Kathy L
AU - Buckley, Michael J.
AU - Henry, Rodger F
AU - Dyhring, Tino
AU - Ahring, P.
AU - Meyer, Michael
PY - 2006
DA - 2006/12/01
PB - American Chemical Society (ACS)
SP - 7843-7853
IS - 26
VL - 49
PMID - 17181167
SN - 0022-2623
SN - 1520-4804
ER -
Cite this
BibTex (up to 50 authors)
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@article{2006_Frost (née Pac,
author = {Jennifer M Frost (née Pac and William H. Bunnelle and Karin R Tietje and David C Anderson and Lynne E Rueter and Peter Curzon and Carol S. Surowy and Jianquo Ji and Jerome F. Daanen and Kathy L Kohlhaas and Michael J. Buckley and Rodger F Henry and Tino Dyhring and P. Ahring and Michael Meyer},
title = {Synthesis and Structure−Activity Relationships of 3,8-Diazabicyclo[4.2.0]octane Ligands, Potent Nicotinic Acetylcholine Receptor Agonists},
journal = {Journal of Medicinal Chemistry},
year = {2006},
volume = {49},
publisher = {American Chemical Society (ACS)},
month = {dec},
url = {https://doi.org/10.1021/jm060846z},
number = {26},
pages = {7843--7853},
doi = {10.1021/jm060846z}
}
Cite this
MLA
Copy
Frost (née Pac, Jennifer M., et al. “Synthesis and Structure−Activity Relationships of 3,8-Diazabicyclo[4.2.0]octane Ligands, Potent Nicotinic Acetylcholine Receptor Agonists.” Journal of Medicinal Chemistry, vol. 49, no. 26, Dec. 2006, pp. 7843-7853. https://doi.org/10.1021/jm060846z.