5-HT1A and 5-HT2A receptor affinity and functional profile of some N-[3-(4-aryl-1-piperazinyl)propyl] derivatives of indolin-2(1H)-one, quinolin-2(1 H)-one and isoquinolin-1(2H)-one. Part 30: Structure-activity relationship studies of CNS agents.
A series of new 1-aryl-4-propylpiperazines containing the modified terminal amide fragment 9, 15-19, 21, 23 and 25 were synthesized and their 5-HT1A and 5-HT2A receptor affinities were determined. All the compound were highly potent 5-HT1A receptor ligands with a diverse 5-HT2A receptor affinity. It was found that the 5-HT2A receptor affinity depends on the dipole moment and lipophilicity of amide moiety. Compound 9b was found to be a 5-HT2A receptor antagonist and a weak 5-HT1A receptor agonist.
Mokrosz
M J
MJ
Department of Medicinal Chemistry, Polish Academy of Sciences, Kraków, Poland.
Mokrosz
J L
JL
Duszyńska
B
B
Dereń-Wesołek
A
A
Kłodzińska
A
A
Kowalski
P
P
Charakchieva-Minol
S
S
Tatarczyńska
E
E
Kowalska
T
T
Majka
Z
Z
Chojnacka-Wójcik
E
E
Misztal
S
S
D017371:8-Hydroxy-2-(di-n-propylamino)tetralin / Q000378:metabolism; D000662:Amphetamines / Q000037:antagonists & inhibitors / Q000494:pharmacology; D000818:Animals; D001522:Behavior, Animal / Q000187:drug effects; D001667:Binding, Competitive / Q000187:drug effects; D055598:Chemical Phenomena; D002627:Chemistry, Physical; D006624:Hippocampus / Q000187:drug effects / Q000378:metabolism; D066298:In Vitro Techniques; D007211:Indoles / Q000138:chemical synthesis* / Q000494:pharmacology; D007546:Isoquinolines / Q000138:chemical synthesis* / Q000494:pharmacology; D007650:Ketanserin / Q000378:metabolism; D007700:Kinetics; D008297:Male; D051379:Mice; D010879:Piperazines / Q000138:chemical synthesis* / Q000494:pharmacology; D015363:Quinolones / Q000138:chemical synthesis* / Q000494:pharmacology; D011869:Radioligand Assay; D051381:Rats; D017208:Rats, Wistar; D011985:Receptors, Serotonin / Q000187:drug effects / Q000378:metabolism*; D012702:Serotonin Antagonists / Q000138:chemical synthesis* / Q000494:pharmacology; D017366:Serotonin Receptor Agonists / Q000138:chemical synthesis* / Q000494:pharmacology
D000662:Amphetamines; D007211:Indoles; D007546:Isoquinolines; D010879:Piperazines; D015363:Quinolones; D011985:Receptors, Serotonin; D012702:Serotonin Antagonists; D017366:Serotonin Receptor Agonists; D017371:8-Hydroxy-2-(di-n-propylamino)tetralin; D007650:Ketanserin; C015952:4-iodo-2,5-dimethoxyphenylisopropylamine