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

• Project/Area Number: 16K18844
• Research Category: Grant-in-Aid for Young Scientists (B)
• Allocation Type: Multi-year Fund
• Research Field: Chemical pharmacy
• Research Institution: Kobe 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: ¥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.

Research Products

• [Journal Article] Photosensitization of fluorofuroxans and its application to the development of visible light-triggered nitric oxide donor (2017)
  • 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
  • Peer Reviewed
• [Journal Article] Synthesis of cyanofuroxans from 4-nitrofuroxans via C-C bond forming reactions (2017)
  • 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
  • Peer Reviewed
• [Journal Article] Synthesis of Enantiomerically Pure (8S,9S,10R,6Z)-Trihydroxyoctadec-6-enoic Acid (2017)
  • 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
  • Peer Reviewed
• [Journal Article] Stynthesis of alkynyl furoxans. Rare carbon-carbon bond forming reaction on a furoxan ring (2017)
  • 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
  • Peer Reviewed / Int'l Joint Research / Acknowledgement Compliant
• [Journal Article] Study on the photo-induced nitric oxide-releasing ability of 4-alkoxy furoxans (2017)
  • 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
  • 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
• [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
• [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
• [Presentation] Development of catalytic photochemical reactions using carbazole platform (2017)
  • 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
  • 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
• [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
• [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
• [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
• [Presentation] Development of catalytic photochemical reactions using carbazole platform (2017)
  • Author(s): Ryosuke Matsubara
  • Organizer: MPI-KobeU-RIKEN Joint Symposium
  • Place of Presentation: 神戸
  • Year and Date: 2017-02-21
  • 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
  • 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
• [Presentation] Development of Novel Photo-labile Protecting Group for Cyano Group (2017)
  • 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
• [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
• [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
• [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
  • 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
• [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
• [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
• [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
• [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
  • 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/