[en] An electrostatic interaction related to a favourable position of the distal phenyl ring and a phenylalanine residue in the binding pocket would explain the higher 5-HT1A affinity of a 4-phenyl-1,2,3,6-tetrahydropyridine (THP) analogue compared to the corresponding 4-phenylpiperazine analogue. To explore a possible reinforcement of this interaction to increase the affinity for 5-HT1A receptors, different 4-substituted-phenyl analogues were synthesized and tested. The most important increase of affinity is obtained with two electron-donating methyl groups in position 3 and 5
Research center :
Centre Interfacultaire de Recherche du Médicament - CIRM
Disciplines :
Pharmacy, pharmacology & toxicology Chemistry
Author, co-author :
Liégeois, Jean-François ; Université de Liège - ULiège > Département de pharmacie > Chimie pharmaceutique
Lespagnard, Marc
Meneses Salas, Elsa
Mangin, Floriane
Scuvée-Moreau, Jacqueline ; Université de Liège - ULiège > Département des sciences biomédicales et précliniques > Pharmacologie
Dilly, Sébastien ; Université de Liège - ULiège > Département des sciences biomédicales et précliniques > Pharmacologie
Language :
English
Title :
Enhancing a CH-pi interaction to increase the affinity for 5-HT1A receptors
Publication date :
2014
Journal title :
ACS Medicinal Chemistry Letters
eISSN :
1948-5875
Publisher :
American Chemical Society, Washington, United States - District of Columbia
Volume :
5
Pages :
358-362
Peer reviewed :
Peer Reviewed verified by ORBi
Funders :
F.R.S.-FNRS - Fonds de la Recherche Scientifique [BE] ULg FSR - Université de Liège. Fonds spéciaux pour la recherche [BE]
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