Asymmetric α-Substituted Phenethylamines. III. The Synthesis and Analgesic Activity of optically Pure (S)- and (R)-1-Aryl-2-phenylethylamines
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概要
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(1S, 1'S)- and (1R, 1'R)-1-aryl-N-2'-hydroxy-1'-isopropylethyl-2-(4-substituted phenyl) ethylamines (7-13 and 18-23) were synthesized by the asymmetric reaction of (E)-(S)- and (E)-(R)-N-(2-hydroxy-1-isopropylethyl) arylmethylideneamines with Grignard reagents. The products showed 100% optical purities ; their absolute configurations were determined by means of circular dichroism. These optically pure chiral amines were converted into hydrochlorides and then evaluated for analgesic activity in the acetic acid-induced mouse-writhing assay. Among these compounds, the hydrochlorides of 9 (1S : 1'S, Ar=2-thienyl, R=H), 13 (1S : 1'S, Ar=2-thienyl, R=MeO), 19 (1R : 1'R, Ar=4-methoxyphenyl, R=H), 20 (1R : 1'R, Ar=2-thienyl, R=H), and 23 (1S : 1'S, Ar=2-thienyl, R=OH) showed inhibition of the writhing ; they were about equipotent with (-)-pentazocine hydrochloride. Moreover, the hydrochlorides of 8 (1S : 1'S, Ar=4-methoxyphenyl, R=H), 13 (1S : 1'S, Ar=2-thienyl, R=MeO), 18 (1R : 1'R, Ar=phenyl, R=H), 19 (1R : 1'R, Ar=4-methoxyphenyl, R=H), 20 (1R : 1'R, Ar=2-thienyl, R=H), and 21 (1R : 1'R, Ar=2-thienyl, R=MeO) were not antagonized by (-)-naloxone hydrochloride.
- 社団法人日本薬学会の論文
- 1983-05-25
著者
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高橋 浩
Faculty Of Pharmaceutical Science Hoshi University
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鈴木 雄二
Kaken Pharmaceutical Co., Ltd.
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鈴木 雄二
Hoshi College Of Pharmacy
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千田 康裕
Institute of Medicinal Chemistry, Hoshi University
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柳浦 才三
Faculty of Pharmaceutical Sciences, Hoshi University
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増田 千春
Kaken Pharmaceutical Co., Ltd.
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増田 千春
Kaken Pharmaceutical Co. Ltd.
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千田 康裕
Institute Of Medicinal Chemistry Hoshi University
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柳浦 才三
星薬料大学・薬理学教室
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柳浦 才三
Department Of Pharmacology Hoshi College Of Pharmacy
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