Synthetic study on biological active natural products by means of Ugi reaction
Project/Area Number |
23390007
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Research Category |
Grant-in-Aid for Scientific Research (B)
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Allocation Type | Single-year Grants |
Section | 一般 |
Research Field |
Chemical pharmacy
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Research Institution | University of Shizuoka |
Principal Investigator |
KAN Toshiyuki 静岡県立大学, 薬学部, 教授 (10221904)
|
Co-Investigator(Kenkyū-buntansha) |
HAMASHIMA Yoshitaka 静岡県立大学, 薬学部, 教授 (40333900)
ASAKAWA Tomohiro 静岡県立大学, 薬学部, 助教 (80571257)
|
Project Period (FY) |
2011-04-01 – 2014-03-31
|
Project Status |
Completed (Fiscal Year 2013)
|
Budget Amount *help |
¥17,550,000 (Direct Cost: ¥13,500,000、Indirect Cost: ¥4,050,000)
Fiscal Year 2013: ¥5,330,000 (Direct Cost: ¥4,100,000、Indirect Cost: ¥1,230,000)
Fiscal Year 2012: ¥5,330,000 (Direct Cost: ¥4,100,000、Indirect Cost: ¥1,230,000)
Fiscal Year 2011: ¥6,890,000 (Direct Cost: ¥5,300,000、Indirect Cost: ¥1,590,000)
|
Keywords | Ugi反応 / FR901483 / TAN1251A / イソニトリル / SB-203207 / MFPA / C-H挿入反応 / 全合成 / レモノマイシン / アルカロイド / TAN1251 / 免疫抑制活性 |
Research Abstract |
The Ugi four-component condensation (Ugi 4CC) has been widely employed since it provides various alfa-amino amide derivatives by a simple experimental procedure under mild conditions. Recently, we have been developed novel isonitrile, which possessed odorless nature as well as readily convertible C-terminal amide of Ugi adducts. In this research, total synthesis of potent immunosuppressant FR901483 and TAN1251A, which possessed the subtype selective affinity against the muscarinic receptors have been accomplished by means of Ugi reaction with utilizing our novel isonitrile.
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Report
(4 results)
Research Products
(118 results)
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[Journal Article] Neuroprotective effect of nobiletin on cerebral ischemia-reperfusion injury in transient middle cerebral artery-occluded rats2014
Author(s)
N. Yasuda, T. Ishii, D. Oyama, T. Fukuta, Y. Agato, A. Sato, K. Shimizu, T. Asai, T. Asakawa, T. Kan, S. Yamada, Y. Ohizumi, N. Oku
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Journal Title
Brain Res
Volume: 1559
Pages: 46-54
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[Journal Article] The "Fairy" of Fairy Rings and Its Metabolite Exist in a Novel Purine Metabolic Pathway in Plants2014
Author(s)
J. Choi, T. Ohnishi, Y. Yamakawa, S. Takeda, S. Sekiguchi, W. Maruyama, K. Yamashita, T. Suzuki, A. Morita, T. Ikka, R. Motohashi, Y. Kiriiwa, H. Tobina, T. Asai, S. Tokuyama, H. Hirai, N. Yasuda, K. Noguchi, T. Asakawa, S. Sugiyama, T. Kan, H. Kawagishi
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Journal Title
Angew. Chem. Int. Ed
Volume: 53
Pages: 1552-1552
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[Journal Article] The Source of “Fairy Rings”: 2-Azahypoxanthine and its Metabolite Found in a Novel Purine Metabolic Pathway in Plants2014
Author(s)
J. Choi, T. Ohnishi, Y. Yamakawa, S. Takeda, S. Sekiguchi, W. Maruyama, K. Yamashita, T. Suzuki, A. Morita, T. Ikka, R. Motohashi, Y. Kiriiwa, H. Tobina, T. Asai, S. Tokuyama, H. Hirai, N. Yasuda, K. Noguchi, T. Asakawa, S. Sugiyama, T. Kan, and H. Kawagishi
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Journal Title
Angew. Chem. Int. Ed.
Volume: 53
Issue: 7483
Pages: 1552-1552
DOI
NAID
Related Report
Peer Reviewed
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[Journal Article] Enantioselective Synthesis of SB-2032072014
Author(s)
Yasuo Hirooka, Kazutada Ikeuchi, Yuichiro Kawamoto, Yusuke Akao, Takumi Furuta, Tomohiro Asakawa, Makoto Inai, Toshiyuki Wakimoto, Tohru Fukuyama and Toshiyuki Kan
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Journal Title
Org. Lett.
Volume: 16
Issue: 6
Pages: 1646-1646
DOI
Related Report
Peer Reviewed
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[Journal Article] Physicochemical and biopharmaceutical characterization of amorphous solid dispersion of nobiletin, a citrus polymethoxylated flavone, with improved hepatoprotective effects2013
Author(s)
S. Onoue, T. Nakamura, A. Uchida, K. Ogawa, K. Yuminoki, N. Hashimoto, A. Hiza, Y. Tsukaguchi, T. Asakawa, T. Kan, S. Yamada
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Journal Title
Euro. J. Pharm. Sci
Volume: 49
Pages: 453-460
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[Journal Article] Physicochemical and biopharmaceutical characterization of amorphous solid dispersion of nobiletin, a citrus polymethoxylated flavone, with improved hepatoprotective effects2013
Author(s)
Satomi Onoue, Tatsuya Nakamura, Atsushi Uchida, Kazunori Ogawa, Kayo Yuminoki, Naofumi Hashimoto, Aiki Hiza, Yuta Tsukaguchi, Tomohiro Asakawa, Toshiyuki Kan, Shizuo Yamada
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Journal Title
Euro. J. Pharm. Sci.
Volume: 49
Issue: 4
Pages: 453-453
DOI
Related Report
Peer Reviewed
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[Journal Article] Effects of Green Tea Catechins on Cytochrome P450 2B6, 2C8, 2C19, 2D6 and 3A Activities in Human Liver and Intestinal Microsomes2013
Author(s)
Misaka, Shingen; Kawabe, Keisuke; Onoue, Satomi; Werba, Jose Pablo; Giroli, Monica; Tamaki, Sekihiro; Kan, Toshiyuki; Kimura, Junko; Watanabe, Hiroshi; Yamada, Shizuo
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Journal Title
Drug Metabolism and Pharmacokinetics
Volume: 28
Issue: 3
Pages: 244-249
DOI
NAID
ISSN
1347-4367, 1880-0920
Related Report
Peer Reviewed
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[Journal Article] Stereocontrolled Total Synthesis of (+)- UCS1025A2012
Author(s)
K. Uchida, T. Ogawa, Y. Yasuda, H. Mimura, T. Fujimoto, T. Fukuyama, T. Wakimoto, T. Asakawa, Y. Hamashima, T. Kan
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Journal Title
Angew. Chem., Int. Ed
Volume: 51
Pages: 12850-12853
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[Journal Article] 3, 3', 4', 5, 5'-Pentahydroxyflavone is a potent inhibitor of amyloid fibril formation2012
Author(s)
H. Ushikubo, S. Watanabe, Y. Tanimoto, K. Abe, A. Hiza, T. Ogawa, T. Asakawa, T. Kan, T. Akaishi
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Journal Title
Neurosci. Lett
Volume: 513
Pages: 51-56
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[Journal Article] Furan Fatty Acid as an Anti-inflammatory Component from Green-Lipped Mussel, Perna canaliculus2011
Author(s)
T. Wakimoto, H. Kondo, H. Nii, K. Kimura, Y. Egami, Y. Oka, M. Yoshida, E. Kida, Y. Ye, S. Akahoshi, T. Asakawa, K. Matsumura, H. Ishida, H. Nukaya, K. Tsuji, T. Kan, I. Abe
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Journal Title
Proc. Natl. Acad. Sci. USA
Volume: 108
Pages: 17533-17537
Related Report
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[Journal Article] PET Imaging Investigation of Nobiletin Based on a Practical Total Synthesis2011
Author(s)
T. Asakawa, A. Hiza, M. Nakayama, M. Inai, D. Oyama, H. Koide, K. Shimizu, T. Wakimoto, N. Harada, H. Tsukada, N. Oku, T. Kan
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Journal Title
Chem. Commun
Volume: 47
Pages: 2868-2870
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[Journal Article] Concise synthesis of catechin probes enabling analysis and imaging of EGCg2011
Author(s)
A. Yoshida, Y. Hirooka, Y. Sugata, M. Nitta, T. Manabe, S. Ido, K. Murakami, R. K. Saha, T. Suzuki, M. Ohshima, A. Yoshida, K. Itoh, K. Shimizu, N. Oku, T. Furuta, T. Asakawa, T. Wakimoto, T. Kan
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Journal Title
Chem. Commun
Volume: 47
Pages: 1794-1796
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[Journal Article] Practical synthesis of natural plant-growth regulator 2-azahypoxanthine, its derivatives, and biotin-labeled probes
Author(s)
K. Ikeuchi, R. Fujii, S. Sugiyama, T. Asakawa, M. Inai, Y. Hamashima, J. Choi, T. Suzuki, H. Kawagishi, T. Kan
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Journal Title
Org. Biomol. Chem
Volume: (in press)
NAID
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[Presentation] アクロメリン酸B の全合成2013
Author(s)
朝比奈彩, 大内仁志, 浅川倫宏, 稲井誠, 濱島義隆, 菅敏幸
Organizer
第30回有機合成化学セミナー
Place of Presentation
岡山
Year and Date
2013-09-18
Related Report
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[Presentation] TAN1251C の合成研究2013
Author(s)
長坂洋祐, 升田明孝, 苅山真美, 稲井誠, 浅川倫宏, 濱島義隆, 菅敏幸
Organizer
日本薬学会第133年会
Place of Presentation
横浜
Year and Date
2013-03-30
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[Presentation] Total Synthesis of Acromelic Acid A and B2013
Author(s)
Hitoshi Ohuchi, Aya Asahina, Tomohiro Asakawa, Makoto Inai, Yoshitaka Hamashima, Toshiyuki Kan
Organizer
13th International Conference on the Chemistry of Antibiotics and other bioactive compounds
Place of Presentation
Yamanashi
Related Report
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[Presentation] Total synthesis of (–)-sphingofungin E2013
Author(s)
Kazutada Ikeuchi, Moemi Hayashi, Tomohiro Yamamoto, Makoto Inai, Tomohiro Asakawa, Yoshitaka Hamashima, Toshiyuki Kan
Organizer
13th International Conference on the Chemistry of Antibiotics and other bioactive compounds
Place of Presentation
Yamanashi
Related Report
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[Presentation] Total synthesis of Palmerolide A2013
Author(s)
Akinori Kawanishi, Yoshiyuki Aihara, Harei Sasaki, Aya Asahina, Takeshi Murata, So Iwata, Makoto Inai, Tomohiro Asakawa, Yoshitaka Hamashima, Toshiyuki Kan
Organizer
13th International Conference on the Chemistry of Antibiotics and other bioactive compounds
Place of Presentation
Yamanashi
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[Presentation] TAN1251C の合成研究2012
Author(s)
長坂洋祐, 升田明孝, 岩永耕治, 浅川倫宏, 濱島義隆, 横島 聡, 福山 透, 菅 敏幸
Organizer
日本病院薬剤師会東海ブロック・日本薬学会東海支部合同学術大会
Place of Presentation
岐阜
Year and Date
2012-11-18
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