Synthesis and Radioligand Binding Studies of C-5- and C-8-Substituted 1-(3,4-Dimethoxybenzyl)-2,2-dimethyl-1,2,3,4-tetrahydroisoquinoliniums as SK Channel Blockers Related to N-Methyl-laudanosine and N-Methyl-noscapine
Publication type: Journal Article
Publication date: 2005-07-01
scimago Q1
wos Q1
SJR: 1.801
CiteScore: 11.5
Impact factor: 6.8
ISSN: 00222623, 15204804
PubMed ID:
16033276
Drug Discovery
Molecular Medicine
Abstract
The synthesis and the (125)I-apamin binding studies of original C-5- and C-8-substituted 1-(3,4-dimethoxy-benzyl)-2,2-dimethyl-1,2,3,4-tetrahydroisoquinoliniums and 1-(3,4-dimethoxy-benzyl)-6,6-dimethyl-4,5,6,7-tetrahydrothieno[2,3-c]pyridiniums were performed in order to find a reversible and selective SK channel blocker structurally related to N-methyl-laudanosine and N-methyl-noscapine. A bulky alkyl substituent in the C-8 position of the tetrahydroisoquinoline produces a clear increase in the affinity for the apamin sensitive binding sites. The presence of an electron-withdrawing group in the C-5 and C-8 positions is not a suitable substitution for the affinity of drugs structurally related to N-methyl-laudanosine. Thiophenic analogues and 8-methoxy derivatives possess a poor affinity for the apamin sensitive binding sites. Electrophysiological studies performed with the most effective compound showed a blockade of the apamin sensitive afterhyperpolarization in rat dopaminergic neurons.
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Graulich A. et al. Synthesis and Radioligand Binding Studies of C-5- and C-8-Substituted 1-(3,4-Dimethoxybenzyl)-2,2-dimethyl-1,2,3,4-tetrahydroisoquinoliniums as SK Channel Blockers Related to N-Methyl-laudanosine and N-Methyl-noscapine // Journal of Medicinal Chemistry. 2005. Vol. 48. No. 15. pp. 4972-4982.
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Graulich A., Scuvée-Moreau J., Seutin V., Li??geois J. F. Synthesis and Radioligand Binding Studies of C-5- and C-8-Substituted 1-(3,4-Dimethoxybenzyl)-2,2-dimethyl-1,2,3,4-tetrahydroisoquinoliniums as SK Channel Blockers Related to N-Methyl-laudanosine and N-Methyl-noscapine // Journal of Medicinal Chemistry. 2005. Vol. 48. No. 15. pp. 4972-4982.
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TY - JOUR
DO - 10.1021/jm049025p
UR - https://doi.org/10.1021/jm049025p
TI - Synthesis and Radioligand Binding Studies of C-5- and C-8-Substituted 1-(3,4-Dimethoxybenzyl)-2,2-dimethyl-1,2,3,4-tetrahydroisoquinoliniums as SK Channel Blockers Related to N-Methyl-laudanosine and N-Methyl-noscapine
T2 - Journal of Medicinal Chemistry
AU - Graulich, Amaury
AU - Scuvée-Moreau, Jacqueline
AU - Seutin, Vincent
AU - Li??geois, J. F.
PY - 2005
DA - 2005/07/01
PB - American Chemical Society (ACS)
SP - 4972-4982
IS - 15
VL - 48
PMID - 16033276
SN - 0022-2623
SN - 1520-4804
ER -
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@article{2005_Graulich,
author = {Amaury Graulich and Jacqueline Scuvée-Moreau and Vincent Seutin and J. F. Li??geois},
title = {Synthesis and Radioligand Binding Studies of C-5- and C-8-Substituted 1-(3,4-Dimethoxybenzyl)-2,2-dimethyl-1,2,3,4-tetrahydroisoquinoliniums as SK Channel Blockers Related to N-Methyl-laudanosine and N-Methyl-noscapine},
journal = {Journal of Medicinal Chemistry},
year = {2005},
volume = {48},
publisher = {American Chemical Society (ACS)},
month = {jul},
url = {https://doi.org/10.1021/jm049025p},
number = {15},
pages = {4972--4982},
doi = {10.1021/jm049025p}
}
Cite this
MLA
Copy
Graulich, Amaury, et al. “Synthesis and Radioligand Binding Studies of C-5- and C-8-Substituted 1-(3,4-Dimethoxybenzyl)-2,2-dimethyl-1,2,3,4-tetrahydroisoquinoliniums as SK Channel Blockers Related to N-Methyl-laudanosine and N-Methyl-noscapine.” Journal of Medicinal Chemistry, vol. 48, no. 15, Jul. 2005, pp. 4972-4982. https://doi.org/10.1021/jm049025p.