| Project/Area Number |
17K15427
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| Research Category |
Grant-in-Aid for Young Scientists (B)
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| Allocation Type | Multi-year Fund |
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| Research Field |
Chemical pharmacy
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| Research Institution | Meiji Pharmaceutical University |
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Principal Investigator |
Tayu Masanori 明治薬科大学, 薬学部, 助教 (20632780)
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| Project Period (FY) |
2017-04-01 – 2021-03-31
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| Project Status |
Completed (Fiscal Year 2020)
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| Budget Amount *help |
¥4,160,000 (Direct Cost: ¥3,200,000、Indirect Cost: ¥960,000)
Fiscal Year 2019: ¥1,300,000 (Direct Cost: ¥1,000,000、Indirect Cost: ¥300,000)
Fiscal Year 2018: ¥1,300,000 (Direct Cost: ¥1,000,000、Indirect Cost: ¥300,000)
Fiscal Year 2017: ¥1,560,000 (Direct Cost: ¥1,200,000、Indirect Cost: ¥360,000)
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| Keywords | スルホニウム / 芳香族求核置換反応 / スルホキシド / 有機硫黄化学 / C-H官能基化 / 硫黄 / 複素環 / 有機化学 / 天然物合成 |
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| Outline of Final Research Achievements |
A method for direct functionalization of electron-rich aromatic rings was developed with a sulfonium species derived from sulfoxide and acid anhydride. In this reaction, the attack of the aromatic ring on a sulfonium species generated in situ forms the aryl sulfonium species. Subsequently, the substrate is functionalized by the nucleophilic aromatic substitution reaction (SNAr reaction) with the nucleophile. When indole was used as a substrate, which is a representative of electron-rich aromatic rings, various nucleophiles were introduced at the 2-position of indole selectively. Furthermore, the same reaction proceeded in the case of benzene derivatives possessing electron-donating groups.
Since this reaction causes an SNAr reaction on an electron-rich aromatic ring, it is expected to be a new methodology for constructing the core skeleton of bioactive compounds and organic functional molecules.
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| Academic Significance and Societal Importance of the Research Achievements |
本研究を通して、医薬品の開発において重要な骨格である芳香環に１工程で官能基を導入できる方法論を開発した。特に「活性の約束された骨格」と言われるインドールの２位を直接的に官能基化できるため、インドール系生物活性物質の合成における有用な方法論である。
さらに、通常は電子不足な芳香環上で起こるSNAr反応を電子豊富な芳香環上で行えるため、学術的に見ても大変興味深く、芳香環の化学の発展に寄与する知見を含んでいる。
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