The Syntheses and β-Adrenoceptor Activities of N-Substituted 2-Amino-5,6-dihydroxy-1,2,3,4-tetrahydro-1-naphthalenols

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概要

• 論文の詳細を見る

• A series of N-substituted 2-amino-5,6-dihydroxy-1,2,3,4-tetrahydro-1-naphthalenols (1), which are comformationally rigid derivatives of adrenergic catecholamine, were synthesized via three routes ; namely, the synthetic route in which the final step is 1) the reduction of 1-carbonyl group, 2) N-substitution by reductive alkylation of 2-amino group, or 3) removal of protecting groups of the catechol moiety. Several pairs of 1,2-cis and trans isomers of 1 were prepared by stereoselective reactions or by separation of each stereoisomer with column chromatography or fractional crystallization. Thus, transamino alcohol (9-trans) was afforded by reduction of 2-amino-5,6-dibenzyloxy-3,4-dihydro-1 (2H)-naphthalenone (13) with sodium borohydride, while the cis isomer (9-cis) was obtained from 7,8-dibenzyloxy-1,2-dihydronaphthalene (19) via an aziridine intermediate. Several of 1 exhibited excellent β_2-adrenoceptor activity superior to l-isoproterenol, the trans derivative being more potent than the cis isomer.

• 社団法人日本薬学会の論文
• 1977-11-25

著者

• 伊藤 克己

  Pharmaceutical Research Laboratories Iii Pharmaceutical Research Division Takeda Chemical Industries

• 伊藤 克己

  Central Research Division, Takeda Chemical Industries, Ltd.,

• 杉原 弘貞

  Central Research Division, Takeda Chemical Industries, Ltd.,

• 岡 良和

  Central Research Division, Takeda Chemical Industries, Ltd.

• 伊藤 克巳

  武田薬品工業

• 西川 正夫

  Chemical Research Laboratories, Central Research Division, Takeda Chemical Industries, Ltd.

• 栗木 久

  Central Research Division Takeda Chemical Industries Ltd.

• 伊藤 克已

  Central Research Division Takeda Chemical Industries Ltd.

• 西川 正夫

  Central Research Division, Takeda Chemical Industries, Ltd.

• 本橋 道生

  Central Research Division, Takeda Chemical Industries, Ltd.

• 稲富 信博

  Central Research Division, Takeda Chemical Industries, Ltd.

• 稲富 信博

  Central Research Division Takeda Chemical Industries Ltd.

• 岡 良和

  Chemistry Laboratories Central Research Division Takeda Chemical Industries Ltd.

• 杉原 弘貞

  Pharamaceutical Research Laboratories I Pharmaceutical Research Division Takeda Chemical Industries

• 杉原 弘貞

  Central Research Division Takeda Chemical Industries. Ltd.

• 西川 正夫

  Central Research Division Takeda Chemical Industries Ltd.

• 本橋 道生

  Central Research Division Takeda Chemical Industries Ltd.

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