Green chemistry oriented synthesis of biologically active natural products and structure-activity relationships
| Project/Area Number |
17590014
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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 |
Chemical pharmacy
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| Research Institution | Tokyo University of Pharmacy and Life Sciences |
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Principal Investigator |
AOYAGI Yutaka Tokyo University of Pharmacy & Life Sciences, School of Pharmacy, Lecturer, 薬学部, 講師 (70212389)
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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 |
¥3,300,000 (Direct Cost: ¥3,300,000)
Fiscal Year 2006: ¥500,000 (Direct Cost: ¥500,000)
Fiscal Year 2005: ¥2,800,000 (Direct Cost: ¥2,800,000)
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| Keywords | Green chemistry / biologically active natural products / diterpene / cytotoxicity / structure-activity relationship / 生理活性 / NF-κB / リパーゼTL / マイクロウェーブ / 環状ヘキサデプシペプチドGE3 / grandione / ent-kaurene / triptolide |
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| Research Abstract |
The results in this project aimed at 'Green Chemistry' are as follows :
1. To discover new biologically active natural products, we explored chemical constituents from higher plants (Labiatae, Coriaceae, Rubiaceae, and Podocarpaceae) using HPLC attached with reversed phase column and aqueous solvent systems. As a results, Some new sesqui-and diterpenes were isolated.
2. Some cytotoxic analogues were synthesized from natural products, isolated from Rabdosia excisa, Perovskia abrotanoides, Coriaria japonica, Tricalysia dubia, and Tripterygium wilfordii. The structure-activity relationships (SAR) between the structures of ent-kaurene type, isetexane type, and abietane type natural products and their semisynthetic analogues and cytotoxic activity were discussed. The microwave oven was used for preparation of semisynthetic analogues aimed at 'Green Chemistry'.
3. The kinetic resolution of secondary alcohols with lipase TL were carried out to produce optically pure secondary alcohols. One of the secondary alcohols was converted to piperazic acids in semi-large scale. Now we are trying to synthesize a natural hexadepsipeptide GE3, which includes both enatiomers of piperazic acids.
4. The facile palladium-catalyzed synthesis of pyrroles and indoles, which are important medicinal molecule skeletons, was developed.
5. The nonproteogenic amino acids were synthesized from Garner aldehydes as a chiral pool.
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Report
(3 results)
Research Products
(25 results)
