Structure-activity relationships of non-peptide vasopressin V1a antagonists: 1-(1-multi-substituted benzoyl 4-piperidyl)-3,4-dihydro-2(1H)-quinolinones.
During our systematic studies on the arginine vasopressin receptor V1a-antagonistic activity of 1-(1-benzoyl substituted 4-piperidyl)-3,4-dihydro-2(1H)-quinolinones, we found a general substituent effect on the benzene ring. Hydrogen-bonding ability at the ortho position was especially important for enhancement of the affinity of multi-substituted analogs. Details of the syntheses and structure-activity relationships for this series are presented.
Kondo
K
K
Second Institute of New Drug Research, Otsuka Pharmaceutical Co., Ltd., Tokushima, Japan.
Ogawa
H
H
Nakaya
K
K
Tominaga
M
M
Yabuuchi
Y
Y
D000818:Animals; D065092:Antidiuretic Hormone Receptor Antagonists; D002462:Cell Membrane / Q000187:drug effects / Q000378:metabolism; D006860:Hydrogen Bonding; D066298:In Vitro Techniques; D008099:Liver / Q000187:drug effects / Q000378:metabolism; D010880:Piperidines / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D015363:Quinolones / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D051381:Rats; D013329:Structure-Activity Relationship
D065092:Antidiuretic Hormone Receptor Antagonists; D010880:Piperidines; D015363:Quinolones