The Synthesis of 2,5-Diamino-6-hydroxy-1,2,3,4-tetrahydro-1-naphthalenol Derivatives
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概要
- 論文の詳細を見る
A series of 2-substituted amino-5-amino-6-hydroxy-1,2,3,4-tetrahydro-1-naphthalenols (2) was synthesized starting with 6-methoxy-3,4-dihydro-1 (2H)-naphthalenone (3). Thus, 6-hydroxy-tetralone (4), prepared by demethylation of 3,was nitrated to give a mixture of 5-nitro (5) and 7-nitro (6) derivatives. Compound 5 was led to the oxime tosylate (9) via compounds 7,8. Neber rearrangement of 9 into α-amino ketone (10) followed by reduction with sodium borohydride afforded trans-2-amino-6-benzyloxy-5-nitro-1,2,3,4-tetrahydro-1-naphthalenol (11), from which compounds 2a, 2b and 2d-r were derived. The 2-methylamino derivative (2c) was prepared via two alternative routes. Most of the compounds 2 exhibited potent β-adrenoceptor agonistic activity with considerable β_2-selectivity. However, compound 24,a position isomer of 2d which was prepared from 6 by the similar procedures, showed no β-adrenoceptor activity.
- 社団法人日本薬学会の論文
- 1977-11-25
著者
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岡 良和
Central Research Division, Takeda Chemical Industries, Ltd.
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西川 正夫
Chemical Research Laboratories, Central Research Division, Takeda Chemical Industries, Ltd.
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栗木 久
Central Research Division Takeda Chemical Industries Ltd.
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三宅 昭夫
Central Research Division, Takeda Chemical Industries, Ltd.
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西川 正夫
Central Research Division, Takeda Chemical Industries, Ltd.
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多田 憲生
Central Research Division, Takeda Chemical Industries, Ltd.
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多田 憲生
Central Research Division Takeda Chemical Industries Ltd.
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岡 良和
Chemistry Laboratories Central Research Division Takeda Chemical Industries Ltd.
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三宅 昭夫
Chemistry Laboratories Central Research Division Takeda Chemical Industries Ltd.
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三宅 昭夫
Central Research Division Takeda Chemical Industries Ltd.
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西川 正夫
Central Research Division Takeda Chemical Industries Ltd.
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