[2-(omega-phenylalkyl)phenoxy]alkylamines: synthesis and dual dopamine2 (D2) and 5-hydroxytryptamine2 (5-HT2) receptor antagonistic activities.
A series of [2-(omega-phenylalkyl)phenoxy]alkylamines was synthesized and their 5-hydroxytryptamine2 (5-HT2) and/or dopamine2 (D2) receptor antagonistic activities were examined in vitro. [2-(4-Phenylbutyl)phenoxy]alkylamines showed strong inhibition of both 5-HT2 and D2 receptors. In particular, [2-(4-Phenylbutyl)phenoxy]-methylpiperidine derivatives, 10b, 10i and 10q, exhibited potent inhibition. The structure-activity relationships in this series of compounds are discussed.
Tanaka
N
N
Medicinal Chemistry Research Laboratories, Sankyo Co., Ltd., Tokyo, Japan.
Goto
R
R
Ito
R
R
Hayakawa
M
M
Ogawa
T
T
Fujimoto
K
K
D000588:Amines / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D000818:Animals; D065127:Dopamine D2 Receptor Antagonists; D009682:Magnetic Resonance Spectroscopy; D008297:Male; D051379:Mice; D009119:Muscle Contraction / Q000187:drug effects; D009131:Muscle, Smooth, Vascular / Q000187:drug effects; D010880:Piperidines / Q000138:chemical synthesis* / Q000494:pharmacology; D051381:Rats; D017207:Rats, Sprague-Dawley; D044402:Receptor, Serotonin, 5-HT2A; D011985:Receptors, Serotonin / Q000187:drug effects; D012702:Serotonin Antagonists / Q000138:chemical synthesis* / Q000494:pharmacology; D013329:Structure-Activity Relationship; D013623:Tail / Q000098:blood supply; D014661:Vasoconstriction / Q000187:drug effects
C112271:1-ethyl-3-(2-(4-(3-methoxyphenyl)butyl)phenoxymethyl)piperidine; C112272:1-methyl-3-(2-(4-(3-methoxyphenyl)butyl)phenoxymethyl)piperidine; C112270:1-methyl-3-(2-(4-phenylbutyl)phenoxymethyl)piperidine; D000588:Amines; D065127:Dopamine D2 Receptor Antagonists; D010880:Piperidines; D044402:Receptor, Serotonin, 5-HT2A; D011985:Receptors, Serotonin; D012702:Serotonin Antagonists