Geduninおよび7―deacetoxy―7α―hydroxygeduninの16位酸化還元反応によるアナログ合成について

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  • Synthesis of analogues through redox reactions at position 16 of Gedunin and 7―Deacetoxy―7α―hydroxygedunin
  • Geduninオヨビ7―deacetoxy―7α―hydroxygeduninノ16イサンカカンゲンハンノウニヨルアナログゴウセイニツイテ

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Of the gedunin-type limonoids obtained from Chinese toon, or Cedrela sinensis Juss. (Meliaceae), gedunin (1)1 is a substance that can be isolated in relatively large quantities. Acetylating gedunin (1) readily results in 7―deacetoxy―7α―hydroxygedunin (2). A previous study2 obtained gedunin analogues by reducing the 1―en―3―one structure of the A ring of gedunin (1), but no studies have obtained analogues by reducing the carbonyl group at position 16 on the D ring of gedunin (1) or 7―deacetoxy―7α―hydroxygedunin (2). In order to determine the chemical reactivity of lactone on the D ring of gedunin (1) and 7―deacetoxy―7α―hydroxygedunin (2), the current authors facilitated redox reactions at position 16. This allowed the synthesis of 2 known compounds, 7―oxogedunin (5) and 3β―hydroxygedunin (9), as well as 5 new analogues (compounds 3, 4, 6, 7, and 8), as reported here. In order to determine the reactivity of gedunin (1), an attempt was made to reduce the substance with LiBH4 and NaBH4. LiBH4 and NaBH4 reduced the ketone at position 3 as well as the lactone-carbonyl group at position 16, yielding a hemiacetal. Further reduction failed to result in a 16―methylol form, indicating that this hemiacetal structure is highly stable. When compound 8 was oxidized with MnO2, the hemiacetal hydroxyl group at position 16 was more readily oxidized than the allyl alcohol at position 3. Limonoid analogues not found in nature were synthesized in order to determine the cytotoxic activity of different functional groups against tumor cells, and the cytotoxic activity of these compounds against P―388 murine leukemia cells was examined. In compounds 3―8, the carbonyl group at position 16 of the D ring of gedunin (1) was oxidized or reduced, and results indicated that these compounds lacked cytotoxic activity for the most part.

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