93(P10) アクロナイシンおよび関連化合物の化学反応(ポスター発表の部)

DOI

書誌事項

タイトル別名
  • 93(P10) CHEMICAL REACTIONS OF ACRONYCINE AND RELATED COMPOUNDS

説明

Acronycine (1) is an alkaloid isolated from the bark of the Australian scrub ash Baurella simplicifolia (ENDL.) Hartley (syn. Acronychia baueri SCOTT) (Rutaceae). When 1 was treated with hot methanolic HCl, two dimers (3,4), a trimer(6), two tetramers (7, 9) and two pentamers (8, 10) of noracronycine (2) were obtained.Two of these seven compounds (4, 9) possessed a rearranged partial structure. The dimeric compound (3) was obtained selectively in 41% yield when 2 was treated with conc. H_2SO_4-MeOH (1:1) at r.t. On the other hand, when norisoacronycine (5) was treated with hot methanolic HCl, a dimeric compound (17) was obtained. The structure of this compound was elucidated by comparison of the ^1H and ^<13>C NMR spectra of this compound with those of 3 and 4. By treatment of dihydronoracronycine (11) with conc. H_2SO_4 at r.t., dihydronorisoacronycine (12) and dihydronoralloacronycine (14) were obtained together with 1,3-dihydroxy-10-methylacridone (13) and 15. It was reported that noracronycine (2) was obtained in quantitative yield when the HCl salt of acronycine was heated at 140℃. On the other hand, when it was heated at 250℃, various acridone derivatives were obtained and one of the main products was dihydronorisoacronycine (12). In this reaction, four novel acridone derivatives 20-23 were obtained. Cytotoxic activities of 16 acridone derivatives obtained through these experiments were evaluated and it was found that 1,3-dihydroxy-10-methylacridone (13) and 1,3-dihydroxy-2,10-dimethylacridone (20) showed activity against VLB resistant KB cells (KB-VI).

収録刊行物

詳細情報 詳細情報について

  • CRID
    1390001206078513920
  • NII論文ID
    110006679821
  • DOI
    10.24496/tennenyuki.38.0_553
  • ISSN
    24331856
  • 本文言語コード
    ja
  • データソース種別
    • JaLC
    • CiNii Articles
  • 抄録ライセンスフラグ
    使用不可

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