Stereoselective synthesis of cis- and trans-3-amino-4-chromanols.

• 杉原 弘貞

• 三野 安

抄録

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 (LiBH₃CN), 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 β₂-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.

収録刊行物

• ＣＨＥＭＩＣＡＬ　＆　ＰＨＡＲＭＡＣＥＵＴＩＣＡＬ　ＢＵＬＬＥＴＩＮ

  ＣＨＥＭＩＣＡＬ　＆　ＰＨＡＲＭＡＣＥＵＴＩＣＡＬ　ＢＵＬＬＥＴＩＮ 25 (5), 859-866, 1977

  公益社団法人 日本薬学会

キーワード

• β<SUB>2</SUB>-stimulant

詳細情報

• CRID: 1390282679147070848
• NII論文ID: 110003622495
• NII書誌ID: AA00602100
• DOI: 10.1248/cpb.25.859
• ISSN: 13475223
• ISSN: 00092363
• PubMed: 45506
• Web Site: http://www.jstage.jst.go.jp/article/cpb1958/25/5/25_5_859/_pdf
• Web Site: https://search.jamas.or.jp/link/ui/1978031261
• 本文言語コード: en
• データソース種別:
  • JaLC
  • Crossref
  • PubMed
  • CiNii Articles
• 抄録ライセンスフラグ: 使用不可