[Novel phenoxyalkylamine derivatives. VI. Synthesis and alpha-blocking activity of alpha-[(phenoxyethylamino)propyl]-alpha-phenylacetonitrile derivatives].
alpha-[(Phenoxyethylamino)propyl]-alpha-(4-methoxyphenyl) acetonitrile derivatives possessing methyl, bromo, nitro, amino or various sulfonamide groups at 3-position on ring A and an alkoxy group on ring B were synthesized. Their alpha-blocking activities were tested. The activity of 5-[1-cyano-4-[[2-(2-ethoxyphenoxy) ethyl]amino]-1-isopropylbutyl]-2-methoxy-benzenesulfonamide (15a) and 5-[1-cyano-4-[[2-(5-fluoro-2-methoxyphenoxy)ethyl] amino]-1-isopropylbutyl]-2-methoxybenzenesulfonamide (15c) was close to that of prazosin, a typical alpha-blocker. Structure-activity relationship of these derivatives is also stated.
Sakurai
S
S
Central Research Laboratories, Hokuriku Seiyaku Co., Ltd., Fukui, Japan.
Okada
F
F
Mitani
K
K
Yasuda
S
S
Kato
H
H
Ito
Y
Y
D000097:Acetonitriles / Q000138:chemical synthesis* / Q000493:pharmacokinetics / Q000494:pharmacology; D000317:Adrenergic alpha-Antagonists; D000818:Animals; D066298:In Vitro Techniques; D008297:Male; D011817:Rabbits; D051381:Rats; D011919:Rats, Inbred Strains; D011954:Receptors, Dopamine / Q000378:metabolism; D013329:Structure-Activity Relationship; D013449:Sulfonamides / Q000138:chemical synthesis* / Q000493:pharmacokinetics / Q000494:pharmacology; D000096926:Benzenesulfonamides
D000097:Acetonitriles; D000317:Adrenergic alpha-Antagonists; D011954:Receptors, Dopamine; D013449:Sulfonamides; C067761:5-(1-cyano-4-((2-(2-ethoxyphenoxy)ethyl)amino)-1-isopropylbutyl)-2-methoxybenzenesulfonamide; D000096926:Benzenesulfonamides; C067762:5-(1-cyano-4-((2-(5-fluoro-2-methoxyphenoxy)ethyl)amino)-1-isopropylbutyl)-2-methoxybenzenesulfonamide