N-クロロアミドを用いたサイト選択C-H塩化により,クロロリスオクリミドの合成が可能
Ryan K Quinn1, Zef A Könst2, Sharon E Michalak2
1Department of Chemistry, The University of North Carolina at Chapel Hill , Chapel Hill, North Carolina 27599, United States.
Journal of the American Chemical Society
|December 24, 2015
まとめ
この研究は,N-クロロアミドを用いてアリファティックC-H結合を塩素化するための選択的方法を導入する. クロロリスオクリミドのような 複雑な分子の効率的な合成を可能にします 潜在的な癌治療薬です
科学分野:
- 有機化学
- 合成方法論
- 薬剤化学
背景:
- アリファティックC−H結合の機能化は有機合成に不可欠である.
- アルカン塩素化のための既存の方法は,しばしば選択的でないか,範囲が限られている.
- サイト選択C-H機能化の開発は,現代化学における重要な課題である.
研究 の 目的:
- アリファティックC−H結合の分子間機能化のための実用的でサイト選択的な方法を開発する.
- この新しい方法論を生物学的に重要な分子の合成に適用する.
- 合成された化合物の抗がん性を探るためだ
主な方法:
- アリファティックC-H結合のサイト選択的塩素化のために利用可能なN-クロロアミド.
- クロロリスソクリミドの短時間合成を 開発した
- スクラレオリドのグラムスケールC-H塩化を用いた.
主要な成果:
- 高位選択性を持つアルキル塩化物の有用な化学的収量を達成した.
- C-H機能化における一般的な課題である基質不飽和に対する耐性が実証されている.
- クロロリスソクリミドと類似物を 合成した
結論:
- 開発されたN-クロロアミド媒介のC-H塩化は,有機合成のためのユニークで高度に選択的なツールを提供します.
- 方法論は,クロロリスソクリミドの合成によって示される複雑な分子への実行可能な経路を提供します.
- 予備的な生物学的測定は,メラノーマと前立腺がんの細胞系に対するクロロリスオクリミドおよびその類似体の適度な活性を示唆している.
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