Synthetic Reaction in Aqueous Media U sing Unprotected Amino Acid as a Starting Material
| Project/Area Number |
17590016
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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 | Toho University |
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Principal Investigator |
YOKOYAMA Yuusaku Toho University, Faculty of Pharmaceutical Sciences, Associate Professor (10095325)
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| Project Period (FY) |
2005 – 2007
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| Project Status |
Completed (Fiscal Year 2007)
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| Budget Amount *help |
¥3,710,000 (Direct Cost: ¥3,500,000、Indirect Cost: ¥210,000)
Fiscal Year 2007: ¥910,000 (Direct Cost: ¥700,000、Indirect Cost: ¥210,000)
Fiscal Year 2006: ¥800,000 (Direct Cost: ¥800,000)
Fiscal Year 2005: ¥2,000,000 (Direct Cost: ¥2,000,000)
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| Keywords | Amino Acid / Decarboxylation / Bromination / Protecting Group / IDO Inhibitor / Tryptophan / Water / Organic Synthesis / 生体分子 / エフェドリン / アミノアルコール / ベンズアルデヒド / 無保護アミノ酸 / 位置選択的 / IDO阻害活性 / 芳香族アミノ酸 / 水溶液 |
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| Research Abstract |
1. We succeeded that the bromination of unprotected aromatic amino adds such as phenylalanine, tyrosine, and phenylglycine using bromoisocyanuric acid sodium salt as a brominating reagent under strong acidic condition (60-90% aqueous solution of H_2SO_4) gave the brominated products in good yields. It is very interesting that protection of amino group was not required in the presence of B r_+ that was possessed oxidizing property.
2. We synthesized the most active inhibitor of indole 2.3-dicorygenase (IDO) by applying the one-step synthetic method of N-acetyltryptophan from indole and serine that was developed by us. Since IDO inhibitors have a big potential as an anti-cancer or anti-Alzheimer disease drug having a new mode of mechanism, we applied this compound to patent last year.
3. In 1942, Akabori reported that the reaction of N-methylalanine with benzaldehyde gave the mixture of diastereoisomer of ephedrine in low yield. By our reinvestigation of this reaction, we found the serious amount of oxazolidine derivative as a by-product that was formed by the reaction of another benzaldehyde with resulted ephedrine. The yield of ephedrine was greatly improved to by heating the reaction mixture with 5% AcOH. The reaction of benzaldehyde having electron donating group on benzene ring gave the aminoalcohol derivatives in excellent yield (up to 87%) . This reaction is not only a new type of the reaction of amino acid that is involved a decarboxylative C-C bond forming reaction on the asymmetric carbon atom but also useful one-pot synthetic reaction aminoalcohol that was involved various important drugs as fundamental skeleton..
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Report
(4 results)
Research Products
(37 results)
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[Journal Article] Chemoselective palladium-catalyzed reaction in aqueous media : Selectivity in the reaction of haloanilines with 1,1-dimethylallyl alcohol2007
Author(s)
Yokoyama, Y., Takagi, T., Hikawa, H., Kaneko, S., Tsubaki, N., Okuno, H
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Journal Title
Advanced Synthesis & Catalysis 349
Pages: 662-668
Description
「研究成果報告書概要(欧文)」より
Related Report
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[Journal Article] Chemistry of Unprotected Amino Acids in Aqueous Solution : Direct Bromination of Aromatic Amino Acids with Bromoisocyanuric acid Sodium Salt under Strong Acidic Condition2006
Author(s)
Yokoyama, Y, Yamaguchi, T, Sato, M, Kobayashi, E, Murakami, Y, Okuno, H
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Journal Title
Chem. Pharm. Bull 54
Pages: 1715-1719
NAID
Description
「研究成果報告書概要(欧文)」より
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[Journal Article] An improved synthesis of optically pure (R)-4-bromo-N-methyl-1-tosyltryptophan derivative, a key intermediate in the synthesis of ergot alkaloids2005
Author(s)
Yokoyama, Y, Hara, R, Kato, N, Murakami, Y, Okuno, H
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Journal Title
Heterocycles 2005
Pages: 1455-1459
Description
「研究成果報告書概要(欧文)」より
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[Presentation] Development of Inhibitors of Indoleamine 2,3-dioxygenase (IDO)2007
Author(s)
Yokoyama,Y., Tsutsumi, K., Akimoto,H., Takikawa, O., Okuno, H
Organizer
6th AFMC International Medicinal Chemistry Symposium
Place of Presentation
Istanbul, Turkey
Description
「研究成果報告書概要(欧文)」より
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[Presentation] Chemoselective Palladium Catalyzed Reaction in Aqueous Media : Selectivity in the Reaction of Bromoanilines with Allylic Alcohol2006
Author(s)
Yokoyama, Y., Takagi, N., Tsubaki, N., Kaneko, N., Hikawa, H., Okuno, H
Organizer
The llth Korea-Japan Joint Symposium on Drug Design And Development
Place of Presentation
Jeju Island, Korea
Description
「研究成果報告書概要(欧文)」より
Related Report
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[Presentation] Chemoselective Palladium Catalyzed Reaction in Aqueous Media : Selectivity in the Reaction of Bromoanilines with Allylic Alcohol2006
Author(s)
Yokoyama, Y., Takagi, N., Tsubaki, N., Kaneko, N., Hikawa, H., Oktino, H
Organizer
The Tenth International Conference on New Aspects of Organic Chemistry (IKCOC-10)
Place of Presentation
Kyoto, Japan
Description
「研究成果報告書概要(欧文)」より
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[Presentation] Bromoisocyanuric Acid Sodium Salt as a Brominating Reagent for Aromatic Amino Acid under Strong Acidic Condition2005
Author(s)
Yokoyama, Y., Satou, M., Yamaguchi, T., Kobayashi, E., Okuno, H., Murakami, Y
Organizer
20th International Congress of Heterocyclic Chemistry
Place of Presentation
Palermo, Italy
Description
「研究成果報告書概要(欧文)」より
Related Report
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