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Exploratory Study on TriQuinoline, A MInituarized Model of Graphene with Atomic-Sized Defect

Research Project

Project/Area Number 19K22192
Research Category

Grant-in-Aid for Challenging Research (Exploratory)

Allocation TypeMulti-year Fund
Review Section Medium-sized Section 33:Organic chemistry and related fields
Research InstitutionMicrobial Chemistry Research Foundation

Principal Investigator

KUMAGAI Naoya  公益財団法人微生物化学研究会, 微生物化学研究所, 主席研究員 (40431887)

Project Period (FY) 2019-06-28 – 2021-03-31
Project Status Completed (Fiscal Year 2020)
Budget Amount *help
¥6,500,000 (Direct Cost: ¥5,000,000、Indirect Cost: ¥1,500,000)
Fiscal Year 2020: ¥2,600,000 (Direct Cost: ¥2,000,000、Indirect Cost: ¥600,000)
Fiscal Year 2019: ¥3,900,000 (Direct Cost: ¥3,000,000、Indirect Cost: ¥900,000)
Keywordsπ平面 / グラフェン / 強塩基 / キノリン / 非共有結合性相互作用
Outline of Research at the Start

ナノカーボンマテリアルは活発に研究展開されている分子構造体であるが,明示的にデザインされた1原子サイズの空間欠損を有する2次元シート型構造体の合成例は限られている。本研究では,独自にデザインした1原子欠損型平面分子: TQ(TriQuinoline)の化学を展開する。予備的に判明しているTQの物性は構造から単純予測できる常識値とは大きく乖離しており,1原子サイズの空間欠損を有する剛直平面分子の構造がその化学物性に大きく反映されている。本特異分子の物性を実験的に精査し,その構造特性と化学物性の新たな相関パラメータを見出すことで,新奇特異機能を賦与する有益な構造要因として一般化可能と期待される。

Outline of Final Research Achievements

Strategic reconsideration of a synthetic route for TriQuinoline: TQ eventually identified a reproducible scheme en route to TQ, allowing for through investigation of its physicochemical properties. Likely due to its unusual structure, various unexpected properties were revealed, e.g. water-solubility, extraordinary proton affinity, both face-to-face and edge-to-face supramolecular complexation with polyaromatics, as well as DNA intercalation. The last is presumably linked to intriguing anti-proliferative activity on certain kinds of tumor cells, which will be pursued toward the development of novel class of anti-cancer therapeutics in the future.

Academic Significance and Societal Importance of the Research Achievements

本研究により今までに存在しない分子骨格が化学合成され,その構造特性に基づく特殊物性が明らかとなった。強固なプロトン保持能や超分子形成能は,環境中の有害多環式芳香族化合物の選択除去剤開発への応用研究が見込まれ,強力なDNAインターカレーション活性に基づく抗腫瘍活性は,新たな分子骨格を有する新規抗がん剤リードとして更なる研究展開が期待される。未知の分子骨格を探索する萌芽的研究であると同時に,標的化合物を成功裡に導出・合成するに至った本研究はその学術的意義の証明のみならず,今後の人類福祉に資する社会的意義を持つと言える研究成果であったと言える。

Report

(3 results)
  • 2020 Annual Research Report   Final Research Report ( PDF )
  • 2019 Research-status Report
  • Research Products

    (18 results)

All 2021 2020 2019 Other

All Journal Article (5 results) (of which Peer Reviewed: 5 results,  Open Access: 1 results) Presentation (12 results) (of which Int'l Joint Research: 1 results,  Invited: 4 results) Remarks (1 results)

  • [Journal Article] Direct Catalytic Asymmetric Addition of Alkylnitriles to Aldehydes with Designed Nickel-Carbene Complexes2021

    • Author(s)
      Akira Saito, Shinya Adachi, Naoya Kumagai, Masakatsu Shibasaki
    • Journal Title

      Angew. Chem. Int. Ed.

      Volume: 60 Issue: 16 Pages: 8739-8743

    • DOI

      10.1002/anie.202016690

    • Related Report
      2020 Annual Research Report
    • Peer Reviewed
  • [Journal Article] The Different Faces of [Ru(bpy)3Cl2] and fac[Ir(ppy)3] Photocatalysts: Redox Potential Controlled Synthesis of Sulfonylated Fluorenes and Pyrroloindoles from Unactivated Olefins and Sulfonyl Chlorides2020

    • Author(s)
      Santosh Kisan Pagire , Naoya Kumagai, Masakatsu Shibasaki
    • Journal Title

      Org. Lett.

      Volume: 22 Issue: 20 Pages: 7853-7858

    • DOI

      10.1021/acs.orglett.0c02760

    • Related Report
      2020 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Direct Catalytic Asymmetric Addition of α‐Fluoronitriles to Aldehydes2020

    • Author(s)
      Pandur Venkatesan Balaji, Zhao Li, Akira Saito, Naoya Kumagai, Masakatsu Shibasaki
    • Journal Title

      Chem. Eur. J.

      Volume: 26 Issue: 67 Pages: 15524-15527

    • DOI

      10.1002/chem.202004743

    • Related Report
      2020 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Design, Synthesis, and Application of Multiboron Heterocycle to Direct Amidation Catalyst2020

    • Author(s)
      Noda Hidetoshi、Shibasaki Masakatsu、Kumagai Naoya
    • Journal Title

      Journal of Synthetic Organic Chemistry, Japan

      Volume: 78 Issue: 10 Pages: 971-978

    • DOI

      10.5059/yukigoseikyokaishi.78.971

    • NAID

      130007923156

    • Related Report
      2020 Annual Research Report
    • Peer Reviewed
  • [Journal Article] TriQuinoline2019

    • Author(s)
      Shinya Adachi, Masakatsu Shibasaki, Naoya Kumagai*
    • Journal Title

      Nat. Commun.

      Volume: 10 Issue: 1 Pages: 3820-3820

    • DOI

      10.1038/s41467-019-11818-1

    • Related Report
      2019 Research-status Report
    • Peer Reviewed / Open Access
  • [Presentation] アセトニトリルを基質とする直截型触媒的不斉付加反応の開発2021

    • Author(s)
      齊藤 誠、足立 慎弥、熊谷 直哉、柴崎 正勝,
    • Organizer
      日本化学会第101春期年会
    • Related Report
      2020 Annual Research Report
  • [Presentation] Design, Synthesis, and Properties of TEtraQuinoline (TEQ)2021

    • Author(s)
      Wei Xu, Naoya Kumagai,
    • Organizer
      日本化学会第101春期年会
    • Related Report
      2020 Annual Research Report
  • [Presentation] 非活性オレフィンとスホニルクロリドの光触媒反応によるスルホニル化フルオレンとピロロインドールの合成2021

    • Author(s)
      PAGIRE Santosh、熊谷 直哉、柴崎 正勝,
    • Organizer
      日本化学会第101春期年会
    • Related Report
      2020 Annual Research Report
  • [Presentation] 特殊へテロ環の化学2020

    • Author(s)
      熊谷 直哉
    • Organizer
      有機合成化学講習会
    • Related Report
      2020 Annual Research Report
    • Invited
  • [Presentation] アルドール反応 古典とモダン、ヘテロ環を楽しむ有機化学2020

    • Author(s)
      熊谷 直哉
    • Organizer
      九州大学
    • Related Report
      2020 Annual Research Report
    • Invited
  • [Presentation] ラクしてスライド用3D動画をつくる2020

    • Author(s)
      熊谷 直哉
    • Organizer
      第10回化学フェスタ
    • Related Report
      2020 Annual Research Report
    • Invited
  • [Presentation] 特殊ヘテロ環の化学2020

    • Author(s)
      熊谷 直哉
    • Organizer
      長崎大学
    • Related Report
      2020 Annual Research Report
    • Invited
  • [Presentation] Direct Catalytic Asymmetric Addition of α-Fluoronitriles to Aldehydes2020

    • Author(s)
      Pandur Venkatesan Balaji, Zhao Li, Akira Saito, Naoya Kumagai, Masakatsu Shibasaki
    • Organizer
      反応と合成の進歩シンポジウム
    • Related Report
      2020 Annual Research Report
  • [Presentation] TriQuinoline2019

    • Author(s)
      熊谷直哉
    • Organizer
      日本化学会新領域研究グループ「分子空間化学」第4回研究集会
    • Related Report
      2019 Research-status Report
  • [Presentation] 一原子欠損グラフェンモデルトリキノリンの合成・物性解析2019

    • Author(s)
      足立慎弥、柴崎正勝、熊谷直哉
    • Organizer
      第30回基礎有機化学討論会
    • Related Report
      2019 Research-status Report
  • [Presentation] TriQuinoline2019

    • Author(s)
      Shinya Adachi, Masakatsu Shibasaki, Naoya Kumagai
    • Organizer
      19th Tateshina Conference
    • Related Report
      2019 Research-status Report
  • [Presentation] TriQuinoline and Its O-Embedded Congeners2019

    • Author(s)
      Yuya Ota, Shinya Adachi, Masakatsu Shibasaki, Naoya Kumagai
    • Organizer
      4th International Symposium on Precisely Designed Catalysts with Customized Scaffolding
    • Related Report
      2019 Research-status Report
    • Int'l Joint Research
  • [Remarks] 微生物化学研究会HP

    • URL

      https://www.bikaken.or.jp/laboratories/organic/summary.html

    • Related Report
      2020 Annual Research Report 2019 Research-status Report

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Published: 2019-07-04   Modified: 2022-01-27  

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