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Development of photolabile protective group for nitrile groups and its application to photoinduced NO donor furoxan

Research Project

Project/Area Number 16K18844
Research Category

Grant-in-Aid for Young Scientists (B)

Allocation TypeMulti-year Fund
Research Field Chemical pharmacy
Research InstitutionKobe University

Principal Investigator

Matsubara Ryosuke  神戸大学, 理学研究科, 准教授 (90401223)

Project Period (FY) 2016-04-01 – 2018-03-31
Project Status Completed (Fiscal Year 2017)
Budget Amount *help
¥4,030,000 (Direct Cost: ¥3,100,000、Indirect Cost: ¥930,000)
Fiscal Year 2017: ¥1,560,000 (Direct Cost: ¥1,200,000、Indirect Cost: ¥360,000)
Fiscal Year 2016: ¥2,470,000 (Direct Cost: ¥1,900,000、Indirect Cost: ¥570,000)
Keywords光反応 / カルバゾール / 光感受性保護基 / 光線力学療法 / ニトリル基 / 光化学 / ニトリル / 有機化学
Outline of Final Research Achievements

Light is a traceless external stimuli and light-driven organic reactions find a wide application in various areas. In this project we have succeeded in development of molecular design which enables photo-induced nitrile formation. This development is useful because nitrile is a common functional group in drugs and fuctional molecules. One potent application of this development is a prodrug which has no effect in dark but obtains a healing function upon photo-irradiation. This is so called photodynamic therapy.

Report

(3 results)
  • 2017 Annual Research Report   Final Research Report ( PDF )
  • 2016 Research-status Report
  • Research Products

    (26 results)

All 2018 2017 2016 Other

All Journal Article (5 results) (of which Int'l Joint Research: 2 results,  Peer Reviewed: 5 results,  Acknowledgement Compliant: 2 results) Presentation (20 results) (of which Int'l Joint Research: 2 results,  Invited: 5 results) Remarks (1 results)

  • [Journal Article] Photosensitization of fluorofuroxans and its application to the development of visible light-triggered nitric oxide donor2017

    • Author(s)
      Christopher Peter Seymour, Rei Toda, Motonari Tsubaki, Masahiko Hayashi and Ryosuke Matsubara
    • Journal Title

      J. Org. Chem.

      Volume: 82 Issue: 18 Pages: 9647-9654

    • DOI

      10.1021/acs.joc.7b01709

    • NAID

      120006469078

    • Related Report
      2017 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Synthesis of cyanofuroxans from 4-nitrofuroxans via C-C bond forming reactions2017

    • Author(s)
      Matsubara Ryosuke、Ando Akihiro、Hayashi Masahiko
    • Journal Title

      Tetrahedron Letters

      Volume: 58 Issue: 34 Pages: 3337-3340

    • DOI

      10.1016/j.tetlet.2017.07.015

    • Related Report
      2017 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Synthesis of Enantiomerically Pure (8S,9S,10R,6Z)-Trihydroxyoctadec-6-enoic Acid2017

    • Author(s)
      Srinivas Jogula、Namito Yoichi、Matsubara Ryosuke、Hayashi Masahiko
    • Journal Title

      The Journal of Organic Chemistry

      Volume: 82 Issue: 10 Pages: 5146-5154

    • DOI

      10.1021/acs.joc.7b00376

    • Related Report
      2017 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Stynthesis of alkynyl furoxans. Rare carbon-carbon bond forming reaction on a furoxan ring2017

    • Author(s)
      Matsubara, R.; Eguchi, S.; Ando, A.; Hayashi, M
    • Journal Title

      Org. Biomol. Chem

      Volume: 15 Issue: 9 Pages: 1965-1969

    • DOI

      10.1039/c7ob00181a

    • Related Report
      2016 Research-status Report
    • Peer Reviewed / Int'l Joint Research / Acknowledgement Compliant
  • [Journal Article] Study on the photo-induced nitric oxide-releasing ability of 4-alkoxy furoxans2017

    • Author(s)
      Matsubara, R.; Takazawa, S.; Ando, A.; Hayashi, M.; Tohda, R.; Tsubaki, M
    • Journal Title

      Asian J. Org. Chem

      Volume: 2017 Issue: 5 Pages: 619-626

    • DOI

      10.1002/ajoc.201700030

    • NAID

      120006414035

    • Related Report
      2016 Research-status Report
    • Peer Reviewed / Int'l Joint Research / Acknowledgement Compliant
  • [Presentation] N-アリールカルバゾールを基本骨格とした新規固体蛍光物質の合成2018

    • Author(s)
      飼馬 知明・薮田 達志・内野 隆司・林 昌彦・松原 亮介
    • Organizer
      日本化学会第98春季年会
    • Related Report
      2017 Annual Research Report
  • [Presentation] 効率的なラジカルの生成を目指した有機分子光触媒の開発2018

    • Author(s)
      薮田 達志・Md Idros Ubaidah Afiq・林 昌彦・松原 亮介
    • Organizer
      日本化学会第98春季年会
    • Related Report
      2017 Annual Research Report
  • [Presentation] フロキサンからα-ケトエステルへの光化学的変換2018

    • Author(s)
      江口 修平・林 昌彦・松原 亮介
    • Organizer
      日本化学会第98春季年会
    • Related Report
      2017 Annual Research Report
  • [Presentation] Development of catalytic photochemical reactions using carbazole platform2017

    • Author(s)
      Ryosuke Matsubara
    • Organizer
      3rd International Symposium on Catalysis Toward Green Sustainable Chemistry
    • Place of Presentation
      東京
    • Year and Date
      2017-03-25
    • Related Report
      2016 Research-status Report
    • Int'l Joint Research / Invited
  • [Presentation] アルキニルフロキサン合成法の開発と誘導体化の検討2017

    • Author(s)
      江口 修平・安藤 祥大・林 昌彦・松原 亮介
    • Organizer
      日本化学会第97春季年会
    • Place of Presentation
      横浜
    • Year and Date
      2017-03-17
    • Related Report
      2016 Research-status Report
  • [Presentation] 強力な脱離基を有するフロキサンの合成2017

    • Author(s)
      葛城 裕規・安藤 祥大・江口 修平・林 昌彦・松原 亮介
    • Organizer
      日本化学会第97春季年会
    • Place of Presentation
      横浜
    • Year and Date
      2017-03-17
    • Related Report
      2016 Research-status Report
  • [Presentation] 直接的シアノ化による効率的なシアノフロキサン誘導体合成法の開発2017

    • Author(s)
      安藤 祥大・林 昌彦・松原 亮介
    • Organizer
      日本化学会第97春季年会
    • Place of Presentation
      横浜
    • Year and Date
      2017-03-17
    • Related Report
      2016 Research-status Report
  • [Presentation] 効率的な炭素ラジカルの生成を目指した有機分子光触媒の開発2017

    • Author(s)
      薮田 達志・林 昌彦・松原 亮介
    • Organizer
      日本化学会第97春季年会
    • Place of Presentation
      横浜
    • Year and Date
      2017-03-17
    • Related Report
      2016 Research-status Report
  • [Presentation] Development of catalytic photochemical reactions using carbazole platform2017

    • Author(s)
      Ryosuke Matsubara
    • Organizer
      MPI-KobeU-RIKEN Joint Symposium
    • Place of Presentation
      神戸
    • Year and Date
      2017-02-21
    • Related Report
      2016 Research-status Report
    • Int'l Joint Research / Invited
  • [Presentation] カルバゾールを光触媒として用いる光反応2017

    • Author(s)
      松原亮介
    • Organizer
      2017年度有機光科学研究会
    • Related Report
      2017 Annual Research Report
    • Invited
  • [Presentation] 効率的な炭素ラジカルの生成を目指した有機分子光触媒の開発2017

    • Author(s)
      薮田達志、Afiq Md Idros、林昌彦、松原亮介
    • Organizer
      第34回有機合成化学セミナー
    • Related Report
      2017 Annual Research Report
  • [Presentation] Development of Novel Photo-labile Protecting Group for Cyano Group2017

    • Author(s)
      Afiq Md Idros, Huiying Ma, Masahiko Hayashi, Ryosuke Matsbuara
    • Organizer
      第37回有機合成若手セミナー
    • Related Report
      2017 Annual Research Report
  • [Presentation] 12.新規フロキサン誘導体合成法の開発と光応答性一酸化窒素ドナーへの応用2017

    • Author(s)
      安藤祥大、林昌彦、松原亮介
    • Organizer
      第111回有機合成シンポジウム
    • Related Report
      2017 Annual Research Report
  • [Presentation] 13.効率的な炭素ラジカルの生成を目指した有機分子光触媒の開発2017

    • Author(s)
      薮田達志、Afiq Md Idros、林昌彦、松原亮介
    • Organizer
      第111回有機合成シンポジウム
    • Related Report
      2017 Annual Research Report
  • [Presentation] フロキサンの合成と応用展開2017

    • Author(s)
      松原亮介
    • Organizer
      14.第3回近畿薬学シンポジウム:化学系の若い力
    • Related Report
      2017 Annual Research Report
    • Invited
  • [Presentation] 効率的な炭素ラジカルの生成を目指した有機分子光触媒の開発2016

    • Author(s)
      薮田達志・島田聡之・林昌彦・松原亮介
    • Organizer
      15.第9回有機触媒シンポジウム
    • Place of Presentation
      名古屋
    • Year and Date
      2016-12-01
    • Related Report
      2016 Research-status Report
  • [Presentation] 効率的な炭素ラジカルの生成を目指した有機分子触媒の開発2016

    • Author(s)
      薮田達志・松原亮介・林 昌彦・小堀康博
    • Organizer
      第6回 CSJ化学フェスタ2016
    • Place of Presentation
      船堀
    • Year and Date
      2016-11-14
    • Related Report
      2016 Research-status Report
  • [Presentation] アルキニル基を有するフロキサン合成法の開発とその応用2016

    • Author(s)
      江口修平・松原亮介・安藤祥大・林 昌彦
    • Organizer
      第6回 CSJ化学フェスタ2016
    • Place of Presentation
      船堀
    • Year and Date
      2016-11-14
    • Related Report
      2016 Research-status Report
  • [Presentation] ハロフロキサンの新規合成法の開発と光応答性一酸化窒素ドナーへの応用2016

    • Author(s)
      安藤祥大・松原亮介・髙沢紗緒里・林 昌彦
    • Organizer
      第6回 CSJ化学フェスタ2016
    • Place of Presentation
      船堀
    • Year and Date
      2016-11-14
    • Related Report
      2016 Research-status Report
  • [Presentation] 光誘起電荷移動状態を形成する有機光触媒の開発2016

    • Author(s)
      松原 亮介
    • Organizer
      分子研研究会 「若い世代が創る次世代型分子触媒の開発とその展望」
    • Place of Presentation
      岡崎
    • Year and Date
      2016-11-10
    • Related Report
      2016 Research-status Report
    • Invited
  • [Remarks] 神戸大学大学院理学研究科 有機反応化学研究室

    • URL

      http://www2.kobe-u.ac.jp/~mhayashi/

    • Related Report
      2016 Research-status Report

URL: 

Published: 2016-04-21   Modified: 2019-03-29  

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