Stereoselective Synthesis of cis-and trans-3-Amino-4-chromanols
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概要
- 論文の詳細を見る
3-Alkylamino-(cis-1a-c) and trans-1a-c), 7-hydroxy-3-isopropylamino-(cis-1d and trans-1d), 7,8-dihydroxy-3-isopropylamino-(cis-1e and trans-1e) and 6,7-dihydroxy-3-isopropylamino-4-chromanol (cis-1f) were synthesized. By the use of lithium cyanoborohydride (LiBH_3CN), the reductive N-alkylation of 3-amino-4-chromanones with acetone proceeded smoothly to produce 3-isopropylamino-4-chromanones (12e and 12f) in good yields. Stereoselective hydrogenation of 4-chromanones in a basic or an acidic medium to give trans- or cis-aminoalcohols was discussed on the basis of the thermodynamic stability of the end products. Among the compounds synthesized, 7,8-dihydroxy derivatives showed a strong β_2-stimulating activity, whereas the 6,7-dihydroxy congener was devoid of the activity. The results suggest an important role of the spatial arrangement of functional groups in these catecholamine molecules with regard to their pharmacological properties.
- 公益社団法人日本薬学会の論文
- 1977-05-25
著者
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杉原 弘貞
Medicinal Research Laboratories, Central Research Division, Takeda Chemical Industries, Ltd.
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三野 安
Medicinal Research Laboratories, Central Research Division, Takeda Chemical Industries, Ltd.
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三野 安
Central Research Division, Takeda Chemical Industries, Ltd.
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杉原 弘貞
Pharamaceutical Research Laboratories I Pharmaceutical Research Division Takeda Chemical Industries
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三野 安
Central Research Division Takeda Chemical Industries Ltd.
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