Chemical Modifications on 4-Arylpiperazine-Ethyl Carboxamide Derivatives Differentially Modulate Affinity for 5-HT1A, D4.2, and alpha(2A) Receptors: Synthesis and In Vitro Radioligand Binding Studies
[en] A series of substituted 4-aryl-piperazine ethyl heteroarylcarboxamides were prepared and tested in in vitro radioligand binding studies. The presence of a quinoxaline has a favourable impact in terms of serotonin 5-HT1A versus dopamine D4.2 receptor selectivity. Compounds with a 3-CF3 group at the distal phenyl ring are the most effective in terms of affinity and selectivity for 5-HT1A versus D4.2 receptors. A 4-phenyl-1,2,3,6-tetrahydropyridine in replacement of the corresponding 4-phenyl-piperazine side chain is also favourable not only for the affinity for 5-HT1A and D4.2 receptors but also in some cases for 2A-adrenoceptors.
Research Center/Unit :
CIRM - Centre Interdisciplinaire de Recherche sur le Médicament - ULiège
Disciplines :
Pharmacy, pharmacology & toxicology
Author, co-author :
Graulich, Amaury
Léonard, Marc ; Université de Liège - ULiège > Centre de recherches du cyclotron
Résimont, Mélissa
Huang, Xi-Ping
Roth, Bryan L.
Liégeois, Jean-François ; Université de Liège - ULiège > Département de pharmacie > Chimie pharmaceutique
Language :
English
Title :
Chemical Modifications on 4-Arylpiperazine-Ethyl Carboxamide Derivatives Differentially Modulate Affinity for 5-HT1A, D4.2, and alpha(2A) Receptors: Synthesis and In Vitro Radioligand Binding Studies
Publication date :
2010
Journal title :
Australian Journal of Chemistry
ISSN :
0004-9425
eISSN :
1445-0038
Publisher :
Commonwealth Scientific and Industrial Research Organization Publishing, Australia
Volume :
63
Pages :
56-67
Peer reviewed :
Peer Reviewed verified by ORBi
Funders :
F.R.S.-FNRS - Fonds de la Recherche Scientifique ULg FSR - Université de Liège. Fonds spéciaux pour la recherche
scite shows how a scientific paper has been cited by providing the context of the citation, a classification describing whether it supports, mentions, or contrasts the cited claim, and a label indicating in which section the citation was made.
Bibliography
B. L. Roth, D. L. Sheffler,W. K. Kroeze, Nat. Rev. Drug Discov. 2004, 3, 353. doi:10.1038/NRD1346
R. Morphy, Z. Rankovic, J. Med. Chem. 2005, 48, 6523. doi:10.1021/ JM058225D
M. J. Marino, L. J. S. Knutsen, M.Williams, J. Med. Chem. 2008, 51, 1077. doi:10.1021/JM701094Q
J.-F. Liégeois, L. Eyrolles, J. Bruhwyler, J. Delarge, Curr. Med. Chem. 1998, 5, 77.
Y.-C. Chung, Z. Li, J. Dai, H.Y. Meltzer, J. Ichikawa, Brain Res. 2004, 1023, 54. doi:10.1016/J.BRAINRES.2004.07.009 (Pubitemid 39195334)
J. Ichikawa, H. Ishii, S. Bonaccorso, W. L. Fowler, I. A. O'Laughlin, H. Y. Meltzer, J. Neurochem. 2001, 76, 1521. doi:10.1046/J.1471- 4159.2001.00154.X
J. Ichikawa, Z. Li, Z. J. Dai, J. H. Y. Meltzer, Brain Res. 2002, 956, 349. doi:10.1016/S0006-8993(02)03570-9 (Pubitemid 35351402)
B. L. Roth, S. M. Hanizavareh, A. E. Blum, Psychopharmacology 2004, 174, 17. doi:10.1007/S00213-003-1683-8
P. Hertel, M. V. Fagerquist, T. H. Svensson, Science 1999, 286, 105. doi:10.1126/SCIENCE.286.5437.105 (Pubitemid 29484485)
P. Carato, A. Graulich, N. Jensen, B. L. Roth, J.-F. Liégeois, Bioorg. Med. Chem. Lett. 2007, 17, 1565. doi:10.1016/J.BMCL.2006.12.096 (Pubitemid 46290635)
P. Carato, A. Graulich, N. Jensen, B. L. Roth, J.-F. Liégeois, Bioorg. Med. Chem. Lett. 2007, 17, 1570. doi:10.1016/J.BMCL.2006.12.106 (Pubitemid 46290633)
M. G. Kelly,Y. L. Palmer, US Patent 6344458 2002.
B. R. Chemel, B. L. Roth, B. Armbruster, V. J. Watts, D. E. Nichols, Psychopharmacology 2006, 188, 244. doi:10.1007/S00213-006- 0490-494
M. Pilla, S. Perachon, F. Sautel, F. Garrido, A. Mann, C. G.Wermuth, J.-C. Schwartz, B. J. Everitt, P. Sokoloff, Nature 1999, 400, 371. doi:10.1038/22560 (Pubitemid 29344203)
K. Wicke, J. Garcia-Ladona, Eur. J. Pharmacol. 2001, 424, 85. doi:10.1016/S0014-2999(01)01054-8 (Pubitemid 32718611)
S. Butini, S. Gemma, G. Campiani, S. Franceschini, F. Trotta, M. Borriello, N. Ceres, S. Ros, S. S. Coccone, M. Bernetti, M. De Angelis, M. Brindisi, V. Nacci, I. Fiorini, E. Novellino, A. Cagnotto, T. Mennini, K. Sandager-Nielsen, J. T. Andreasen, J. Scheel-Kruger, J. D.Mikkelsen, C. Fattorusso, J. Med. Chem. 2009, 52, 151. doi:10.1021/JM800689G
J.-F. Liégeois, L. Eyrolles, P. Carato, J. Bruhwyler, J. Géczy, J. Damas, J. Delarge, J. Med. Chem. 2002, 45, 5136. doi:10.1021/JM0104825 (Pubitemid 35278709)
A. Ducarme, M. Neuwels, S. Goldstein, R. Massingham, Eur. J. Med. Chem. 1998, 33, 215. doi:10.1016/S0223-5234(98)80011-1 (Pubitemid 28188258)
A. Reichel, D. J. Begley, Pharm. Res. 1998, 15, 1270. doi:10.1023/ A:1011904311149
T. Salminen, A. Pully, J. Taskinen, J. Pharm. Biomed. Anal. 1997, 15, 469. doi:10.1016/S0731-7085(96)01883-3 (Pubitemid 26384301)
J. Chen, K. Ding, B. Levant, S.Wang, Bioorg. Med. Chem. Lett. 2006, 16, 443. doi:10.1016/J.BMCL.2005.09.053 (Pubitemid 41680644)
L. Santana, E. Uriarte, Y. Fall, M. Teijeira, C. Terán, E. García- Martínez, T. Bo-Ragnar, Eur. J. Med. Chem. 2002, 37, 503. doi:10.1016/S0223-5234(02)01357-0 (Pubitemid 35245173)
J. Nilsson, H. Wikström, A. Smilde, S. Glase, T. Pugsley, G. Cruciani, M. Pastor, S. Clementi, J. Med. Chem. 1997, 40, 833. doi:10.1021/JM9605952 (Pubitemid 27131612)
R. Perrone, F. Berardi, N. A. Colabufo, M. Leopoldo, V. Tortorella, J. Med. Chem. 1998, 41, 4903. doi:10.1021/JM981041X (Pubitemid 28530465)
N. H. Jensen, R. M. Rodriguiz, M. G. Caron, W. C. Wetsel, R. B. Rothman, B. L. Roth, Neuropsychopharmacology 2008, 33, 2303. doi:10.1038/SJ.NPP.1301646
Similar publications
Sorry the service is unavailable at the moment. Please try again later.
This website uses cookies to improve user experience. Read more
Save & Close
Accept all
Decline all
Show detailsHide details
Cookie declaration
About cookies
Strictly necessary
Performance
Strictly necessary cookies allow core website functionality such as user login and account management. The website cannot be used properly without strictly necessary cookies.
This cookie is used by Cookie-Script.com service to remember visitor cookie consent preferences. It is necessary for Cookie-Script.com cookie banner to work properly.
Performance cookies are used to see how visitors use the website, eg. analytics cookies. Those cookies cannot be used to directly identify a certain visitor.
Used to store the attribution information, the referrer initially used to visit the website
Cookies are small text files that are placed on your computer by websites that you visit. Websites use cookies to help users navigate efficiently and perform certain functions. Cookies that are required for the website to operate properly are allowed to be set without your permission. All other cookies need to be approved before they can be set in the browser.
You can change your consent to cookie usage at any time on our Privacy Policy page.
