Synthetic study of bioactive molecules aimed at providing natural products and developing into medicinal chemistry
| Project/Area Number |
16K08180
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| Research Category |
Grant-in-Aid for Scientific Research (C)
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| Allocation Type | Multi-year Fund |
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| Section | 一般 |
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| Research Field |
Chemical pharmacy
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| Research Institution | Hoshi University |
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Principal Investigator |
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| Research Collaborator |
Matsuzawa Akinobu
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| Project Period (FY) |
2016-04-01 – 2019-03-31
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| Project Status |
Completed (Fiscal Year 2018)
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| Budget Amount *help |
¥4,810,000 (Direct Cost: ¥3,700,000、Indirect Cost: ¥1,110,000)
Fiscal Year 2018: ¥1,040,000 (Direct Cost: ¥800,000、Indirect Cost: ¥240,000)
Fiscal Year 2017: ¥1,690,000 (Direct Cost: ¥1,300,000、Indirect Cost: ¥390,000)
Fiscal Year 2016: ¥2,080,000 (Direct Cost: ¥1,600,000、Indirect Cost: ¥480,000)
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| Keywords | 天然有機化合物 / 全合成 / 創薬化学 / boscartin F / cochlearol B / ganocin A / alstoscholarisin A / 天然物 / alstoscholarisine A / 全合成研究 / 誘導体合成 / 創薬化学指向 / 空間ダイバーシティ |
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| Outline of Final Research Achievements |
The asymmetric total synthesis of boscartin F was carried out utilizing Sharpless asymmetric epoxidation, stereoselective I2-mediated iodoetherification, coupling by aldol reaction, ring-clothing metathesis and stereoselective epoxidation. This synthesis was achieved in entioselective and protecting-group-free manner in a longest linear sequence of 10 steps from known compound. For synthetic study of cochlearol B, we have succeeded in construction of a carbon skeleton. In addition to this, we are now constructing tetrahydrofuran ring which is the last ring to finish total synthesis of ganocin A soon.
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| Academic Significance and Societal Importance of the Research Achievements |
本研究で全合成研究の対象とした天然有機化合物は、いずれも特色ある化学構造を有している。boscartin Fは14員環骨格をもち、cochlearol Bおよびganocin Aは立体的な化学構造を有していることから、タンパク質間相互作用を制御する分子として期待できる。今後、スケールアップ合成および誘導体合成を実施し、さらに、シグナル伝達において重要な機能を果たすタンパク質とのin silicoでの結合能評価、合成した天然物および誘導体を用いた生物活性試験等を外部研究室との共同研究を含めて検討し、これまでに制御する薬剤が見出されていない領域での創薬を目指す。
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Report
(4 results)
Research Products
(24 results)
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[Journal Article] Facile Total Synthesis of (+)-Spinoxazine B2018
Author(s)
Mayuko Iwata, Motoi Kuwabara, Akinobu Matsuzawa, and Kazuyuki Sugita
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Journal Title
Chemical and Pharmaceutical Bulletin
Volume: 66
Issue: 12
Pages: 1196-1198
DOI
NAID
ISSN
0009-2363, 1347-5223
Year and Date
2018-12-01
Related Report
Peer Reviewed / Open Access
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[Journal Article] Usefulness for the combination of G-protein- and β-arrestin-biased ligands of μ-opioid receptors: Prevention of antinociceptive tolerance2017
Author(s)
Tomohisa Mori, Naoko Kuzumaki, Takamichi Arima, Michiko Narita, Ryunosuke Tateishi, Takashige Kondo, Yusuke Hamada, Hirotsugu Kuwata, Miho Kawata, Mitsuaki Yamazaki, Kazuyuki Sugita, Akinobu Matsuzawa, Kanae Baba, Takayasu Yamauchi, Kimio Higashiyama, Miki Nonaka, Kanako Miyano, Yasuhito Uezono, Minoru Narita
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Journal Title
Molecular Pain
Volume: 13
Pages: 1-9
DOI
Related Report
Peer Reviewed / Open Access
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