2005 Fiscal Year Final Research Report Summary
Investigation of new biologically active compounds containing a dendrimer skeleton
| Project/Area Number |
15550036
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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 |
Organic chemistry
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| Research Institution | OKAYAMA UNIVERSITY |
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Principal Investigator |
TSUBOI Sadao OKAYAMA UNIVERSITY, Graduate School of Environment, Professor, 大学院環境学研究科, 教授 (00032954)
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| Co-Investigator(Kenkyū-buntansha) |
TAKAGUCHI Yutaka OKAYAMA UNIVERSITY, Graduate School of Environment, Associate Professor, 大学院環境学研究科, 助教授 (10293482)
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| Project Period (FY) |
2003 – 2005
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| Keywords | fullarodendrimer / Darzen's condensation / Pyrones / butenolide / verrcosapyrone A / 3-DPA lactone / anticancer activity / antibiotics |
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| Research Abstract |
This project consists of investigation of the synthesis of biologically active compounds, which can be utilized for new medicines. These materials have dendrimer skeletone and biologically active components. Research interest of head investigator was the synthesis of biologically active compounds for a long time. Another investigator has developed new chemistry of fullarodendrimers. Head investigator synthesized many oxygen-contaning biologically active compounds such as anticancer and antibiotics by Darzen's condensation (reaction of aldehydes and dichloroacetates in the presence of base) as a key step. In this research, head investigator discovered a new synthetic method of alpha-hydroxy butenolides by the treatment of glycidic esters with MgCl_2, and 3-DPA lactone was prepared. Head investigator found out treatment of alpha-chloroglycidic esters (1) with triphenylphosphine gives 3-chloro-2-ketoesters (2). Furthermore, treatment of 1 with potassium acetate gave 2-acetoxy-3-ketoesters (3) newly. By this new reaction, (-)-verrucosapyrone A (4) was synthesized and the absolute configuration of its one carbon was clarified. The structure of 4 is similar to that of pestalotin, of which has an activity of promotor of plant growth. So, many biological activities would be expected. New pyrone synthesis from acetonide-protected glycidate (1) was also reported.
In a future, connection of newly prepared oxygen-containing cyclic compounds with fullarodendrimer will be established, and biological activities of these final products would be investigated.
In this project, many new results were obtained and thirteen papers were published in valuable journals.
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[Journal Article] Novel Synthesis of 4-Halo-3-hydroxy-2-pyrone : One Pot Rearrange- ment-Cyclization Reaction by Magnesium Halide2005
Author(s)
Komiyama, T., Takaguchi, Y., Gubaidullin, A.T., Mamedov, V.A., Litvinov, I.A., Tsuboi, S.
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Journal Title
Tetrahedron 61
Pages: 2541
Description
「研究成果報告書概要(和文)」より
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