Electrochemical oxidation of aromatic compounds towards effective biologically active substances
| Project/Area Number |
17510182
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| Research Category |
Grant-in-Aid for Scientific Research (C)
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| Allocation Type | Single-year Grants |
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| Section | 一般 |
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| Research Field |
Living organism molecular science
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| Research Institution | Keio University |
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Principal Investigator |
HISHIYAMA Shigcru Keio University, Faculty of Science and Technology, Professor, 理工学部, 教授 (20137988)
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| Co-Investigator(Kenkyū-buntansha) |
MAKI Shojiro The University of Electro-communications, Faculty of Electro-communications, Research Associate, 電気通信学部, 助手 (20266349)
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| Project Period (FY) |
2005 – 2006
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| Project Status |
Completed (Fiscal Year 2006)
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| Budget Amount *help |
¥3,500,000 (Direct Cost: ¥3,500,000)
Fiscal Year 2006: ¥1,100,000 (Direct Cost: ¥1,100,000)
Fiscal Year 2005: ¥2,400,000 (Direct Cost: ¥2,400,000)
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| Keywords | phenolic oxidation / natural products / anodic oxidation / diaryl ether / spiroisoxazole / thallium salt / hypervalent iodine / mangostin / ユーリパミド / 抗MRSA / ニトレニウムイオン / 環境対応 / 生理活性 / 有機化学 / 有機電気化学 / 全合成 |
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| Research Abstract |
In the research project, anodic oxidation of phenol and related derivatives provided the following results.
1.In construction of the diaryl ether linkage shared by the isodityrosine-class natural products such as vancomycin, optimization of cyclization reactions employing thallium(III) salt was performed to provide the eurypamide derivative in quantitative yield. It was revealed that the cyclic derivative effectively increased the anti-MRSA activity of imipenem. Electrochemical generation of Tl(III) from Tl(I) was succeeded, and further efforts to make its catalytic system is in progress. In addition, galeon, a cytotoxic diaryl ether derivative of plant origin, was synthesized by controlling halogen-substituent to provide expected cyclization direction, and to introduce a required functional group.
2.Upon comparing with natural verbenachalcone carrying the diaryl ether linkage, synthetic derivatives exhibited effective enhancement or inhibitory activity of NFG-mediated neurite outgrowth from PC12D cell.
3.The absolutely optically active aerothionin, aeroplysinin-1, and their enantiomers were synthesized by diastereomeric-separation techniques.
4.Phenolic oxidation of mangostins provided a series of dienone-type products. Reactivities of phenol functions are evaluated.
5.Anodic oxidation of iodobenzene provided a hyper-valent iodine species, which was used as an effective oxidant.
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Report
(3 results)
Research Products
(32 results)
