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Development and application of the environmental friendly organic synthesis using characteristics of the heterocycle

Research Project

Project/Area Number 20590025
Research Category

Grant-in-Aid for Scientific Research (C)

Allocation TypeSingle-year Grants
Section一般
Research Field Chemical pharmacy
Research InstitutionMukogawa Women's University

Principal Investigator

KAWASAKI Ikuo  Mukogawa Women's University, 薬学部, 准教授 (00234055)

Co-Investigator(Renkei-kenkyūsha) 西出 喜代治  武庫川女子大学, 薬学部, 教授 (10237711)
田渕 裕佳子  武庫川女子大学, 薬学部, 助手 (80509943)
山下 正行  京都薬科大学, 薬学部, 教授 (20239982)
久留米 愛  京都薬科大学, 薬学部, 助手 (40454475)
Project Period (FY) 2008 – 2010
Project Status Completed (Fiscal Year 2010)
Budget Amount *help
¥4,290,000 (Direct Cost: ¥3,300,000、Indirect Cost: ¥990,000)
Fiscal Year 2010: ¥1,040,000 (Direct Cost: ¥800,000、Indirect Cost: ¥240,000)
Fiscal Year 2009: ¥1,300,000 (Direct Cost: ¥1,000,000、Indirect Cost: ¥300,000)
Fiscal Year 2008: ¥1,950,000 (Direct Cost: ¥1,500,000、Indirect Cost: ¥450,000)
Keywords有機合成 / 複素環 / 不斉還元 / リサイクル / イオン性化合物 / イオン液体 / リガンド / 触媒
Research Abstract

A novel chiral ionic ligand which has the structure of the quaternary ammonium salt in the nitrogen containing heterocycle was prepared, and asymmetric reduction of prochiral ketone proceeded well when the ionic ligand with Ru and formic acid as a hydrogen source was used for catalytic asymmetric transfer hydrogenation (CATH). This reaction system of CATH could be expanded to recycling CATH (RCATH) by using ionic liquid as a reaction medium. Thus, I could achieve the development of the environmental friendly organic synthesis used a characteristic of the heterocycle. Furthermore, this reaction system of RCATH could be applied to the synthesis of pharmaceutical useful compound, and I succeeded in the asymmetric synthesis of the pharmaceutical product.

Report

(4 results)
  • 2010 Annual Research Report   Final Research Report ( PDF )
  • 2009 Annual Research Report
  • 2008 Annual Research Report
  • Research Products

    (46 results)

All 2011 2010 2009 2008 Other

All Journal Article (10 results) (of which Peer Reviewed: 10 results) Presentation (29 results) Book (5 results) Remarks (2 results)

  • [Journal Article] Cucurbitacin E as a new inhibitor of cofilin phosphorylation in human leukemia U937 cells, Bioorg.2010

    • Author(s)
      M.Yamashita, 他
    • Journal Title

      Med.Chem.Letters 20

      Pages: 2994-2997

    • Related Report
      2010 Final Research Report
    • Peer Reviewed
  • [Journal Article] Preparation of novel (Z)-4-ylidenebenzo[b]furo[3,2-d][1,3]oxazines and their biological activity2009

    • Author(s)
      I.Kawasaki, 他
    • Journal Title

      Bioorg.Med.Chem. 17

      Pages: 3959-3967

    • Related Report
      2010 Final Research Report
    • Peer Reviewed
  • [Journal Article] Preparation of novel(Z)-4-ylidenebenzo[b]furo[3, 2-d][1, 3]oxazines and their biological activity2009

    • Author(s)
      I.Kawasaki, 他
    • Journal Title

      Bioorg. Med.Chem. 17(11)

      Pages: 3959-3967

    • Related Report
      2009 Annual Research Report
    • Peer Reviewed
  • [Journal Article] A novel transformation of 1-exo-substituted 2a-aroyl-1,2,2a,8b-tetrahydro-3H-benzo[b]cyclobuta[d]pyran-3-ones with sulfoxonium ylide to highly strained 2a-(1-arylethenyl)-1,2,2a,7b-tetrahydrocyclobuta[b]benzofurans2008

    • Author(s)
      I.Kawasaki, 他
    • Journal Title

      Tetrahedron Letters 49

      Pages: 1627-1630

    • Related Report
      2010 Final Research Report
    • Peer Reviewed
  • [Journal Article] Preparation of leukotriene B4 inhibitory active 2- and 3-(2-aminothiazol-4-yl)benzo[b]furan derivatives and their growth inhibitory activity on human pancreatic cancer cells2008

    • Author(s)
      I.Kawasaki, 他
    • Journal Title

      Org.Biomo.Chem. 20

      Pages: 2772-2781

    • Related Report
      2010 Final Research Report
    • Peer Reviewed
  • [Journal Article] Synthesis of 3-substituted isocoumarins and their inhibitory effects on degranulation of RBL-2H3 cells induced by antigen2008

    • Author(s)
      I.Kawasaki, 他
    • Journal Title

      Chem.Pharm.Bull. 56

      Pages: 1264-1269

    • NAID

      110006878895

    • Related Report
      2010 Final Research Report
    • Peer Reviewed
  • [Journal Article] A novel transformation of 1-exo-substituted 2a-aroyl-1, 2, 2a, 8b-tetrahydro-3H-benzo[b]cyclobuta[d]pyran-3-ones with sulfoxonium ylide to highly strained 2a-(1-arvlethenv)-1,2,2a, 7b-tetrahvdrocvclobuta[b]benzofurans2008

    • Author(s)
      N. D. Yadav, I. Kawasaki, 他
    • Journal Title

      Tetrahedron Letters 49

      Pages: 1627-1630

    • Related Report
      2008 Annual Research Report
    • Peer Reviewed
  • [Journal Article] A novel skeleton transformation of 2a-substituted 2a, 8b-dihydro-3H-benzo[b]cy clobuta[d]pyran-3-ones to 2-(2-oxoethyl)-2H-1-benzopyrans promoted by a combination of ZnI_2, organic base and H_2O2008

    • Author(s)
      N. D. Yadav, I. Kawasaki, 他
    • Journal Title

      Synlett 2008

      Pages: 428-432

    • Related Report
      2008 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Preparation of leukotriene B_4 inhibitory active 2- and 3-(2-aminothiazol-4-yl)benzo[b]furan derivatives and their growth inhibitory activity on human pancreatic cancer cells2008

    • Author(s)
      M. Kuramoto, I. Kawasaki, 他
    • Journal Title

      Organic and Biomolecular Chemistry 6

      Pages: 2772-2781

    • Related Report
      2008 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Synthesis of 3-substitUted isocoumarins and their inhibitory effects on degranu lation of RBL-2H3 cells induced by antigen2008

    • Author(s)
      A. Kurume, I. Kawasaki, 他
    • Journal Title

      Chemical and Pharmaceutical Bulletin 56

      Pages: 1264-1269

    • Related Report
      2008 Annual Research Report
    • Peer Reviewed
  • [Presentation] Redox chemistry of antioxidative dihydropyridine derivatives bearing a pyrazole moiety2010

    • Author(s)
      川崎郁勇, 他
    • Organizer
      2010 International Chemical Congress of Pacific Basin Societies
    • Place of Presentation
      Honolulu
    • Year and Date
      2010-12-15
    • Related Report
      2010 Annual Research Report
  • [Presentation] 光学的に純粋な4-ヒドロキシ-2-ピペコリン酸誘導体の簡便合成法の検討2010

    • Author(s)
      川崎郁勇, 他
    • Organizer
      60回日本薬学会近畿支部大会
    • Place of Presentation
      枚方市
    • Year and Date
      2010-10-30
    • Related Report
      2010 Annual Research Report
  • [Presentation] リサイクル反応を用いる光学活性テルブタリン誘導体の合成研究2010

    • Author(s)
      川崎郁勇, 他
    • Organizer
      60回日本薬学会近畿支部大会
    • Place of Presentation
      枚方市
    • Year and Date
      2010-10-30
    • Related Report
      2010 Annual Research Report
  • [Presentation] イオン液体中でのリサイクル反応による不斉水素移動型還元反応を利用する光学活性テルブタリンの合成研究2010

    • Author(s)
      川崎郁勇, 他
    • Organizer
      日本薬学会第131年会
    • Place of Presentation
      静岡
    • Year and Date
      2010-03-31
    • Related Report
      2010 Annual Research Report 2010 Final Research Report
  • [Presentation] 光学活性4-hydroxy-2-pipecolic acid誘導体の簡便かつ効率的な不斉合成の研究2010

    • Author(s)
      川崎郁勇, 他
    • Organizer
      日本薬学会第131年会
    • Place of Presentation
      静岡
    • Year and Date
      2010-03-31
    • Related Report
      2010 Annual Research Report
  • [Presentation] (Benzo[b]furo[3,2-d][1,3]oxazin-4-ylidene)acetaldehydeからのbenzo[b]furo[3,2-b]pyridine誘導体の合成2010

    • Author(s)
      川崎郁勇, 他
    • Organizer
      日本薬学会第131年会
    • Place of Presentation
      静岡
    • Year and Date
      2010-03-31
    • Related Report
      2010 Annual Research Report
  • [Presentation] イオン液体中でのリサイクル反応による各種ケトン類の不斉水素移動型還元反応を利用する光学活性テルブタリンの不斉合成研究2010

    • Author(s)
      川崎郁勇, 他
    • Organizer
      日本薬学会第130年会
    • Place of Presentation
      岡山
    • Year and Date
      2010-03-28
    • Related Report
      2010 Final Research Report 2009 Annual Research Report
  • [Presentation] 6年制薬学部教育における基礎学力向上のための学習支援の効果2010

    • Author(s)
      川崎郁勇, 他
    • Organizer
      日本薬学会第130年会
    • Place of Presentation
      岡山
    • Year and Date
      2010-03-28
    • Related Report
      2009 Annual Research Report
  • [Presentation] ベンゾフラン骨格を有する三環性化合物の合成とその生物活性2010

    • Author(s)
      川崎郁勇, 他
    • Organizer
      日本薬学会第130年会
    • Place of Presentation
      岡山
    • Year and Date
      2010-03-28
    • Related Report
      2009 Annual Research Report
  • [Presentation] 光学的に純粋な4種の4-hydroxy-2-pipecolic acid誘導体の簡便合成2010

    • Author(s)
      川崎郁勇, 他
    • Organizer
      日本薬学会第130年会
    • Place of Presentation
      岡山
    • Year and Date
      2010-03-28
    • Related Report
      2009 Annual Research Report
  • [Presentation] リサイクル反応を利用する光学活性テルブタリンの合成研究2009

    • Author(s)
      川崎郁勇, 他
    • Organizer
      59回日本薬学会近畿支部大会
    • Place of Presentation
      東大阪
    • Year and Date
      2009-10-24
    • Related Report
      2010 Final Research Report 2009 Annual Research Report
  • [Presentation] Benzo[b]furo[3, 2-d][1, 3]oxazine誘導体の合成とその生物活性2009

    • Author(s)
      田渕裕佳子, 川崎郁勇, 他
    • Organizer
      日本薬学会第129年会
    • Place of Presentation
      京都, 京都国際会館
    • Year and Date
      2009-03-28
    • Related Report
      2008 Annual Research Report
  • [Presentation] 複素環を有するbenzo[b]furan誘導体の合成と生物活性2009

    • Author(s)
      伊東あずさ, 川崎郁勇, 他
    • Organizer
      日本薬学会第129年会
    • Place of Presentation
      京都, 京都国際会館
    • Year and Date
      2009-03-28
    • Related Report
      2008 Annual Research Report
  • [Presentation] 4-Chloro-3-formylbenzo[b]furo[3, 2-b]pyridineからの縮合四環性化合物の合成2009

    • Author(s)
      遠藤千賀子, 川崎郁勇, 他
    • Organizer
      日本薬学会第129年会
    • Place of Presentation
      京都, 京都国際会館
    • Year and Date
      2009-03-28
    • Related Report
      2008 Annual Research Report
  • [Presentation] ジメチルスルホキソニウムメチリドを用いた1, 8b位置換ベンソ[b]シクロブタ[d]ピラン-3-オンの骨格変換反応2009

    • Author(s)
      久留米愛, 川崎郁勇, 他
    • Organizer
      日本薬学会第129年会
    • Place of Presentation
      京都, 京都国際会館
    • Year and Date
      2009-03-28
    • Related Report
      2008 Annual Research Report
  • [Presentation] ベンソフラン骨格をコアとする標臓癌および乳癌治療薬創製研究2009

    • Author(s)
      川崎郁勇, 他
    • Organizer
      平成20年度武庫川女子大学共同研究センターシンポジウム : 受容体分子を標的とする新規制癌剤の創製
    • Place of Presentation
      西宮, 武庫川女子大学
    • Year and Date
      2009-01-31
    • Related Report
      2008 Annual Research Report
  • [Presentation] 抗アレルギー作用を有するthunberginol類の合成と構造活性相関2008

    • Author(s)
      久留米愛, 川崎郁勇, 他
    • Organizer
      平成20年度「戦略的大学連携支援事業」先端科学セミナー京都ケミカルバイオロジーシンポジウム
    • Place of Presentation
      京都, 京都府立大学
    • Year and Date
      2008-12-15
    • Related Report
      2008 Annual Research Report
  • [Presentation] A novel skeleton transformation of 2a-substituted 2a, 8b-dihydro-3H-benzo-[b]cyclobuta[d]pyran-3-ones to 2-(2-oxoethyl)-2H-1-benzopyrans promoted by a combination of ZnI_2-organic base-H_2O2008

    • Author(s)
      K. Tsunoda, I. Kawasaki, 他
    • Organizer
      International Symposium on Integrated Medicinal Science-On the basis of traditional medicine to biomolecular system
    • Place of Presentation
      京都, 京都薬科大学
    • Year and Date
      2008-12-13
    • Related Report
      2008 Annual Research Report
  • [Presentation] Benzo[b]furo[3, 2-d][1, 3]oxazin-4-ylideneacetaldehyde誘導体の合成とその生物活性2008

    • Author(s)
      田渕裕佳子, 川崎郁勇, 他
    • Organizer
      第27回メディシナリーケミストリーシンポジウム
    • Place of Presentation
      大阪, メルパルク大阪
    • Year and Date
      2008-11-26
    • Related Report
      2008 Annual Research Report
  • [Presentation] Thunberginol B及び関連化合物の合成とそれらの抗アレルギー活性2008

    • Author(s)
      久留米愛, 川崎郁勇, 他
    • Organizer
      第27回メディシナリーケミストリーシンポジウム
    • Place of Presentation
      大阪, メルパルク大阪
    • Year and Date
      2008-11-26
    • Related Report
      2008 Annual Research Report
  • [Presentation] ZnI_2-Organic base-H_2Oにより促進される2a位置換2a, 8b-ジヒドロ-3H-ベンソ[b]シクロブタ[d]ピラン-3-オンの新規骨格変換反応2008

    • Author(s)
      久留米愛, 川崎郁勇, 他
    • Organizer
      第38回複素環化学討論会
    • Place of Presentation
      福山, 広島県民文化センターふくやま
    • Year and Date
      2008-11-22
    • Related Report
      2008 Annual Research Report
  • [Presentation] 複素環を有するbenzo[b]furan誘導体の合成と反応2008

    • Author(s)
      伊東あずさ, 川崎郁勇, 他
    • Organizer
      第28回有機合成若手セミナー明日の有機合成を担う人のために
    • Place of Presentation
      吹田, 大阪大学銀杏会館
    • Year and Date
      2008-11-12
    • Related Report
      2008 Annual Research Report
  • [Presentation] 4-Chloro-3-formylbenzo[b]furo[3, 2-b]pyridineからの四環性化合物の合成2008

    • Author(s)
      遠藤千賀子, 川崎郁勇, 他
    • Organizer
      第28回有機合成若手セミナー明日の有機合成を担う人のために
    • Place of Presentation
      吹田, 大阪大学銀杏会館
    • Year and Date
      2008-11-12
    • Related Report
      2008 Annual Research Report
  • [Presentation] イオン液体中で用いる不斉金属触媒の開発とテルブタリン不斉合成への応用2008

    • Author(s)
      川崎郁勇, 他
    • Organizer
      第34回反応と合成の進歩
    • Place of Presentation
      京都(シンポジウム)
    • Year and Date
      2008-11-04
    • Related Report
      2010 Final Research Report
  • [Presentation] イオン液体中で用いる不斉金属触媒の開発とテルブタリン不斉合成への応用2008

    • Author(s)
      川崎郁勇, 他
    • Organizer
      第34回反応と合成の進歩シンポジウム
    • Place of Presentation
      京都, 京都テルサ
    • Year and Date
      2008-11-04
    • Related Report
      2008 Annual Research Report
  • [Presentation] 複素環を有するbenzo[b]furan誘導体の合成と反応2008

    • Author(s)
      伊東あずさ, 川崎郁勇, 他
    • Organizer
      第58回日本薬学会近畿支部大会
    • Place of Presentation
      神戸, 神戸薬科大学
    • Year and Date
      2008-10-25
    • Related Report
      2008 Annual Research Report
  • [Presentation] 4-Chloro-3-formylbenzo[b]furo[3, 2-b]pyridineからの四環性化合物の合成2008

    • Author(s)
      遠藤千賀子, 川崎郁勇, 他
    • Organizer
      第58回日本薬学会近畿支部大会
    • Place of Presentation
      神戸, 神戸薬科大学
    • Year and Date
      2008-10-25
    • Related Report
      2008 Annual Research Report
  • [Presentation] Development of recycling catalytic asymmetric transfer hydrogenation system in ionic liquid2008

    • Author(s)
      川崎郁勇, 他
    • Organizer
      18^<th> International Symposium on Fine Chemistry and Functional Polymers & IUPAC 4^<th> International Symposium on Novel Materials and Synthesis
    • Place of Presentation
      Zhenjiang, China
    • Year and Date
      2008-10-16
    • Related Report
      2010 Final Research Report
  • [Presentation] Development of recycling catalytic asymmetric transfer hydroge nation system in ionic liquid2008

    • Author(s)
      Ikuo Kawasaki, 他
    • Organizer
      18^<th> International Symposium on Fine Chemistry and Functional Polymers & IUPAC 4^<th> International Symposium on Novel Materials and Synthesis
    • Place of Presentation
      Zhenjiang, China
    • Year and Date
      2008-10-16
    • Related Report
      2008 Annual Research Report
  • [Book] 有機医薬品合成化学 ターゲット分子の合成2011

    • Author(s)
      川崎郁勇, 他
    • Publisher
      廣川書店
    • Related Report
      2010 Final Research Report
  • [Book] 有機医薬品合成化学 ターゲット分子の合成2011

    • Author(s)
      池田潔、川崎郁勇, 他
    • Publisher
      廣川書店
    • Related Report
      2010 Annual Research Report
  • [Book] Innovated構造解析プラクティス2010

    • Author(s)
      川崎郁勇, 他
    • Publisher
      京都廣川書店
    • Related Report
      2010 Final Research Report
  • [Book] Innovated構造解析プラクティス2010

    • Author(s)
      桑島博、川崎郁勇, 他
    • Publisher
      京都廣川書店
    • Related Report
      2010 Annual Research Report
  • [Book] 有機化学explorer:有機化学で未来をひらけ2009

    • Author(s)
      川崎郁勇, 他
    • Publisher
      京都廣川書店
    • Related Report
      2010 Final Research Report 2009 Annual Research Report
  • [Remarks] ホームページ

    • URL

      http://ph.mukogawa-u.ac.jp/~yakka1/

    • Related Report
      2010 Final Research Report
  • [Remarks]

    • URL

      http://ph.mukogawa-u.ac.jp/~yakka1/

    • Related Report
      2010 Annual Research Report

URL: 

Published: 2008-04-01   Modified: 2016-04-21  

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