Synthesis of 14, 15-Epoxyisobufadienolides

• 南原 利夫

• 島田 和武

• 合屋 周次郎

抄録

In order to clarify the structure-activity relationship of the cardiotonic steroids the synthesis of the 14, 15-epoxyisobufadienolides, in which C-17 is linked to 6-position of the α-pyrone ring, has been undertaken. When refluxed with triphenyltin hydride in xylene, pregna-14, 16-dien-20-ones underwent selective hydrogenation to yield the corresponding ⊿¹⁴-unsaturated compounds. Condensation with ethyl orthoformate followed by cyclization with malonic acid gave the ⊿¹⁴-isobufadienolides. Subsequent treatment with N-bromoacetamide and then with alumina resulted in formation of the desired 14β, 15β-epoxyisobufadienolides (VIIIa, b). The epimeric 14α, 15α-epoxides (VIa, b) were also prepared with the object of comparing the biological activity.

収録刊行物

• ＣＨＥＭＩＣＡＬ　＆　ＰＨＡＲＭＡＣＥＵＴＩＣＡＬ　ＢＵＬＬＥＴＩＮ

  ＣＨＥＭＩＣＡＬ　＆　ＰＨＡＲＭＡＣＥＵＴＩＣＡＬ　ＢＵＬＬＥＴＩＮ 18 (3), 453-457, 1970

  公益社団法人 日本薬学会

キーワード

• Drug Discovery
• General Chemistry
• General Medicine

詳細情報

• CRID: 1390282679148696832
• NII論文ID: 110003632316
• NII書誌ID: AA00602100
• DOI: 10.1248/cpb.18.453
• ISSN: 13475223
• ISSN: 00092363
• Web Site: http://www.jstage.jst.go.jp/article/cpb1958/18/3/18_3_453/_pdf
• Web Site: https://search.jamas.or.jp/link/ui/1971046359
• 本文言語コード: en
• データソース種別:
  • JaLC
  • Crossref
  • CiNii Articles
• 抄録ライセンスフラグ: 使用不可