強力なチューブリン重合阻害活性を有するオッテリオン類の全合成

• 荒木 宏史

• 加藤 正

  東北薬科大学

書誌事項

タイトル別名

• Total Synthesis of Otteliones Possessing Powerful Tubulin Polymerization Inhibitory Activity
• キョウリョク ナ チューブリン ジュウゴウ ソガイ カッセイ オ ユウスル オッテリオンルイ ノ ゼンゴウセイ

抄録

Otteliones A and B, isolated from the fleshwater plant Ottelia alismoides, were found to exhibit extremely potent growth-inhibitory activity against human cancer cell lines. Structurally, these small-molecule natural products possess a novel bicyclic hydrindane skeleton with four contiguous asymmetric carbon centers, in which the rare and sensitive 4-methylene-2-cyclohexenone substructure is a special characteristic feature. When these natural products were isolated, the relative configuration of ottelione B was determined; however, ottelione A could not been assigned unambiguously. In this article, we describe the first enantioselective total synthesis of (+)-ottelione A, (-)-ottelione B, and (+)-3-epi-ottelione A (the earlier proposed stereostructure of ottelione A) using a flexible synthetic scheme that allows an access to all possible stereostructures of ottelione A. The present total synthesis has fully established the absolute configuration of these natural products. In addition, the cell growth inhibition analysis and tubulin polymerization assay of the synthesized otteliones are also described.

収録刊行物

• 有機合成化学協会誌

  有機合成化学協会誌 67 (9), 909-920, 2009

  公益社団法人 有機合成化学協会

キーワード

• otteliones
• antitumor agents
• tubulin polymerization inhibitors
• natural products
• total synthesis

詳細情報

• CRID: 1390282680288800000
• NII論文ID: 10025400251
• NII書誌ID: AN0024521X
• DOI: 10.5059/yukigoseikyokaishi.67.909
• COI: 1:CAS:528:DC%2BD1MXht1WgtLbI
• ISSN: 18836526
• ISSN: 00379980
• NDL書誌ID: 10384818
• Web Site: http://id.ndl.go.jp/bib/10384818
• Web Site: https://ndlsearch.ndl.go.jp/books/R000000004-I10384818
• 本文言語コード: ja
• データソース種別:
  • JaLC
  • NDL
  • Crossref
  • CiNii Articles
  • KAKEN
• 抄録ライセンスフラグ: 使用不可