Kumagai, Naoya

写真a

Affiliation

Faculty of Pharmacy, Department of Pharmaceutical Sciences 分子創成化学講座 ( Shiba-Kyoritsu )

Position

Professor

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External Links

Career 【 Display / hide 】

  • 2005.04
    -
    2006.03

    harvard University, Departmernt of Chemistry and Chemical Biology, Postdoctoral Fellow

  • 2006.04
    -
    2010.03

    The University of Tokyo, Graduate School of Pharmaceutical Sciences, Assistant Professor

  • 2010.04
    -
    2010.12

    Institute of Microbial Chemistry, Laboratory of Synthetic Organic Chemnistry, Researcher

  • 2010.04
    -
    2017.03

    Rikkyo University, Department of Science, Adjunct Lecturer

  • 2011.01
    -
    2013.03

    Insttitute of Microbial Chemistry, Laboratory of Synthetic Organic Chemistry, Senior Researcher

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Academic Background 【 Display / hide 】

  • 1996.04
    -
    2000.03

    The University of Tokyo, Department of Pharmaceutical Sciences

    University, Graduated

  • 2000.04
    -
    2002.03

    The University of Tokyo, Graduate School of Pharmaceutical Sciences

    Graduate School, Completed, Master's course

  • 2002.04
    -
    2005.03

    The University of Tokyo, Graduate School of Pharmaceutical Sciences

    Graduate School, Completed, Doctoral course

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Academic Degrees 【 Display / hide 】

  • The University of Tokyo, The University of Tokyo, Coursework, 2005.03

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Licenses and Qualifications 【 Display / hide 】

  • Pharmacist, 2000.09

  • senior [first class] radiation protection supervisor, 2012.04

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Research Areas 【 Display / hide 】

  • Nanotechnology/Materials / Structural organic chemistry and physical organic chemistry

  • Life Science / Bioorganic chemistry

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Books 【 Display / hide 】

  • Interplay of diamides and rare earth metals: Specific molecular spaces and catalytic activity

    Kumagai N., Shibasaki M., Designed Molecular Space in Material Science and Catalysis, 2018.01

    　View Summary

    A catalytic system comprising functionalized small diamides and rare earth metals (REs) exerts intriguing catalytic properties that are dictated by dynamic construction of flexible molecular spaces. The dynamic interaction of diamides and REs is characterized by broad applicability to distinct reaction systems as well as notable switchable catalysis. Structural modification of the diamide allows for enhanced intermolecular interactions to afford a self-assembled solid-phase catalyst with a specific molecular space that engages in heterogeneous asymmetric catalysis with a continuous-flow platform.

  • Chiral Bimetallic Lewis Acids

    Shibasaki M., Kumagai N., Topics in Organometallic Chemistry, 2018

    　View Summary

    Here, we review the utility of chiral bimetallic (multimetallic) Lewis acidic complexes in catalytic asymmetric transformations. Bimetallic complexes are endowed with dual catalytic functions that synergistically activate multiple substrates and functionalities. This cooperative activation mode is particularly effective for activating low reactivity substrates in a highly stereoselective manner without the aid of stoichiometric activating reagents. The privileged bimetallic catalysts presented here highlight the importance of catalyst design in the development of widely applicable catalytic systems.

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Papers 【 Display / hide 】

  • DiazaChrysenes (DC): Nitrogen-Containing π-Extended Molecules for Photocatalytic C–H Amination

    Xu W., Iwai A., Nagasaka I., Watanabe S., Tsutsumi R., Kumagai N.

    Organic Letters (American Chemical Society)  27 ( 39 ) 10937 - 10942 2025.10

    Research paper (scientific journal), Joint Work, Last author, Corresponding author, Accepted,  ISSN  15237060

    　View Summary

    We report a new class of nitrogen-containing π-extended heterocycles, DiazaChrysenes (DCs), and their dimeric analogues (dDCs) as metal-free photocatalysts for C–H amination. DCs featuring a quinolino[1,2-c]quinazolin-5-ium core were synthesized via electrophilic amide activation and arylation. The resulting compounds displayed tunable photophysical and redox properties, with CF<inf>3</inf>-substituted DCs enabling the C–H amination of arenes with azoles under visible light and aerobic conditions, achieving yields up to 85%. The reaction tolerated a range of arene and azole substrates without requiring metal salts or additives. In contrast, dDCs exhibited diminished activity, likely due to their extended π-curvature. Computational studies, including NCI, ACID, and NICS analyses, revealed locally aromatic but electronically isolated π-systems and deshielded central 8-membered cores. This work highlights the utility of DC scaffolds as synthetically accessible and redox-tunable organic photocatalysts.

  • Enlarged-TriQuinoline (Enl-TQ): Disparity in Chemical Behaviors by Geometric Scaling of the Trimeric Quinoline Ring System

    Yamashita M., Tsutsumi R., Kobayashi T., Kumagai N.

    Chemistry an Asian Journal (Wiley)  20 ( 17 )  2025.09

    Research paper (scientific journal), Last author, Corresponding author,  ISSN  18614728

    　View Summary

    TriQuinoline (TQ), a quasi-planar cyclic quinoline trimer concatenated at the 2,8-positions in a head-to-tail arrangement, strongly captures a proton at the 12-membered inner cycle and exhibits unusual physicochemical properties, including unexpected water solubility and the ability to engage in complexation with other π-conjugated molecules. In this study, we designed and synthesized its expanded analog, coined Enlarged-TriQuinoline (Enl-TQ), in which three alkyne units are embedded between three quinoline units to acquire an expanded planar 18-membered ring system. DFT calculations and X-ray crystallographic analysis revealed its planar architecture with three inwardly facing pyridinic nitrogen atoms. Despite its structural similarity to TQ, Enl-TQ displayed distinct host capability and photophysical characteristics.

  • iso-TEtraQuinoline (i-TEQ): an inherently chiral N4 macrocyclic quinoline tetramer

    Yagami R., Xu W., Kobayashi T., Nagata Y., Kumagai N.

    Chemical Science (Royal Society of Chemistry)  16 ( 24 ) 10714 - 10721 2025.05

    Research paper (scientific journal), Last author, Corresponding author, Accepted,  ISSN  20416520

    　View Summary

    Chiral macrocycles are attracting growing interest due to their broad applicability as ligands in asymmetric catalysis and as host molecules for chiral recognition. Robustness and high thermodynamic stability can be effectively achieved by strategically linking aromatic panels to construct an axially chiral macrocyclic framework. Cyclic concatenation of four quinoline units affords a fully sp<sup>2</sup>-hybridized, non-planar macrocycle featuring four inwardly oriented, coordinatively active pyridyl nitrogen atoms. The previously reported tetramer TEtraQuinoline (TEQ) exhibits head-to-tail connectivity of its quinoline units, affording an achiral architecture possessing S<inf>4</inf> symmetry. Herein, we report the design and synthesis of iso-TEtraQuinoline (i-TEQ), an inherently chiral analogue featuring head-to-head connectivity at the 2,2′- and 8,8′-positions, which gives rise to a D<inf>2</inf>-symmetric architecture. Detailed comparative investigations of the connectivity isomers i-TEQ and TEQ revealed an array of distinct characteristics, including the overall architecture, intrinsic macrocyclic strain, spatial orientation of nitrogen lone pairs, thermodynamic stability, racemisation behaviour, metal complex stability, and circularly polarised luminescence.

  • DiQuinoline-MonoQuinazoline: A Flat Proton Binder and its Application as a Polyaromatic Hydrocarbon Scavenger and G4 Ligand

    Karimata T., Xu W., Kumagai N.

    Chemistry - A European Journal (Wiley)  31 ( 12 )  2025

    Research paper (scientific journal), Last author, Corresponding author, Accepted,  ISSN  09476539

    　View Summary

    A new miniaturized framework for graphitic material featuring three neighboring pyridinic nitrogen atoms is disclosed. The quinoline/quinazoline hybridized pseudo trimeric macrocycle, DiQuinoline(Q)-MonoQuinazolines(Qz), Q2Qz1, was readily synthesized from the key macrocyclic amide precursor in a modular fashion. Its central cavity strongly captures a proton, and the thus-formed positively charged, highly planar architecture exhibits supramolecular complexation through π-interactions. Q2Qz1, with its unique properties, was applied as a scavenger for toxic polyaromatic hydrocarbons and as a G-quartet ligand for potential therapeutic agent for cancer chemotherapy.

  • Development of Unique Quinoline-Based Macrocyclic Systems and Strategic Applications in Versatile Chemistry

    Kobayashi T., Xu W., Kumagai N.

    Journal of Synthetic Organic Chemistry (有機合成化学協会)  83 ( 5 ) 386 - 394 2025

    Research paper (scientific journal), Last author, Corresponding author, Accepted,  ISSN  00379980

    　View Summary

    Macrocyclic compounds exhibit unique properties due to their large ring─shaped structures, which have captivated chemists in recent decades. These molecules exert specific functions in a multidisciplinary basis, e.g. chemistry, materials science, and biology. Crown ethers, calix [n] arenes, and porphyrinoids, which contain several ether／phenol／pyrrole subunits, represent milestones in these molecular categories with unparalleled functional diversity. In contrast, macrocycles exploiting quinoline as a key unitary element to construct specific macrocyclic architecture have received limited attention and been barely explored. In this report, we summarize the recent advances in oligo─ quinoline macrocycles TriQuinoline (TQ), oxa─TriQuinoline (o─TQ), TEtraQuinoline (TEQ), and indole／quinoline hybrid macrocycle In2Q2. Particular emphasis is placed on the synthesis, structure, and application of these molecules in organometallic and supramolecular chemistry, which may guide new molecular designs in the heterocycle─based macrocycle family.

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Papers, etc., Registered in KOARA 【 Display / hide 】

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Reviews, Commentaries, etc. 【 Display / hide 】

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Presentations 【 Display / hide 】

  • Revisiting C4N4: 蛍光発光メカニズムの計算化学的解明と重金属検出プローブへの応用

    公平実希、川村剛、原渕祐、前田理、熊谷直哉

    [Domestic presentation]  日本化学会第105春季年会, 

    2025.03
    , 

    Oral presentation (general)

  • カルボン酸を基質とした触媒的還元的アミノ化反応の開発

    中村健人、堤亮祐、熊谷直哉

    [Domestic presentation]  日本薬学会第145年会, 

    2025.03
    , 

    Oral presentation (general)

  • キノリンベースドカーボンナノリングの創製

    山下舞、小林透威、熊谷直哉

    [Domestic presentation]  日本薬学会第145年会, 

    2025.03
    , 

    Oral presentation (general)

  • 含窒素大環状4量体群In2Q2およびBIm2Q2の合成・機能探索

    木原和輝、小林透威、木村美玲、Wei Xu、熊谷直哉

    [Domestic presentation]  日本化学会第105春季年会, 

    2025.03
    , 

    Oral presentation (general)

  • キノリンを基盤とした環状及び非環状アミドフォルダマーの創製と機能評価

    武田彩海、Wei Xu、熊谷直哉

    [Domestic presentation]  日本化学会第105春季年会, 

    2025.03
    , 

    Oral presentation (general)

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Research Projects of Competitive Funds, etc. 【 Display / hide 】

  • 軽元素分子触媒戦略によるアミド生産技術の刷新

    2024.12
    -
    2027.03

    科学技術振興機構（JST）, 研究成果最適展開支援プログラム（A-STEP）産学共同 ステージⅠ（育成フェーズ）, Joint research, Principal investigator

  • Expeditious Sophistication of Seed Molecular Entities Aided by Theory and Machine Learning

    2023.04
    -
    2026.03

    学術変革領域研究(B), Principal investigator

  • Diversification of Molecular Functions via Unique Molecular Design

    2023.04
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    2026.03

    基盤研究(B), Principal investigator

  • Porphyrin 2.0: Chemistry of Warped-Porphyrin

    2022.06
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    2024.03

    MEXT,JSPS, Grant-in-Aid for Scientific Research, 挑戦的研究（萌芽）, Principal investigator

  • Strategic Molecular Design Aiming at Streamlined Chemical Transformations

    2020.04
    -
    2023.03

    MEXT,JSPS, Grant-in-Aid for Scientific Research, Grant-in-Aid for Scientific Research (B), Principal investigator

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Awards 【 Display / hide 】

  • Mukaiyama Award

    2023

    Type of Award： International academic award (Japan or overseas)

  • Merck Banyu Lectureship Award（MBLA）

    2018

    Type of Award： International academic award (Japan or overseas)

  • 三井化学触媒科学奨励賞

    2014

    Type of Award： International academic award (Japan or overseas)

  • Thieme Chemistry Journal Award

    2013

    Type of Award： International academic award (Japan or overseas)

  • 文部科学大臣表彰若手科学者賞

    2013

    Type of Award： International academic award (Japan or overseas)

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Courses Taught 【 Display / hide 】

  • STUDY OF MAJOR FIELD (MOLECULAR DESIGN)

    2025

  • SEMINAR (MOLECULAR DESIGN)

    2025

  • RESEARCH FOR BACHELOR'S THESIS 1

    2025

  • PHARMACEUTICAL-ENGLISH SEMINAR

    2025

  • ORGANIC SYNTHESIS

    2025

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