Article (Scientific journals)
Synthesis and in vitro binding studies of substituted piperidine naphthamides. Part I: Influence of the substitution on the basic nitrogen and the position of the amide on the affinity for D-2L, D-4.2, and 5-HT2A receptors
Carato, P.; Graulich, Amaury; Jensen, N. et al.
2007In Bioorganic and Medicinal Chemistry Letters, 17 (6), p. 1565-1569
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Keywords :
D-4.2 receptors; 5-HT2A receptors; antagonist; schizophrenia
Abstract :
[en] A series of 1- and 2-naphthamides has been prepared and tested for in vitro binding to D-2L, D-4.2, and 5-HT2A receptors. Different compounds display selectivity for D-4.2 and 5-HT2A receptors versus D-2L receptors. N-(1-Arylalkyl-piperidin-4-yl) carboxamides have higher affinities than the corresponding N-(4-arylalkylamino-piperidin-1-yl) carboxamide analogues. A benzyl moiety in position 1 of the piperidine in the 2-naphthamide series (2) appears to be the best choice for a favorable interaction with D-4.2 and 5-HT2A receptors. Increasing the linker length between the phenyl ring and the basic nitrogen led to a decreased affinity for these receptors. In the 1-naphthamide series, the most potent D-4.2 ligand (7) possesses a phenylpropyl moiety while its affinity for 5-HT2A receptors is strongly reduced. All compounds with significant affinity for D-4.2 and 5-HT2A receptors were antagonists. (c) 2007 Elsevier Ltd. All rights reserved.
Disciplines :
Pharmacy, pharmacology & toxicology
Chemistry
Author, co-author :
Carato, P.
Graulich, Amaury ;  Université de Liège - ULiège > Chimie pharmaceutique
Jensen, N.
Roth, B. L.
Liégeois, Jean-François ;  Université de Liège - ULiège > Département de pharmacie > Chimie pharmaceutique
Language :
English
Title :
Synthesis and in vitro binding studies of substituted piperidine naphthamides. Part I: Influence of the substitution on the basic nitrogen and the position of the amide on the affinity for D-2L, D-4.2, and 5-HT2A receptors
Publication date :
15 March 2007
Journal title :
Bioorganic and Medicinal Chemistry Letters
ISSN :
0960-894X
eISSN :
1464-3405
Publisher :
Pergamon-Elsevier Science Ltd, Oxford, United Kingdom
Volume :
17
Issue :
6
Pages :
1565-1569
Peer reviewed :
Peer Reviewed verified by ORBi
Available on ORBi :
since 09 January 2009

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