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

Related Websites

External Links
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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 】

  • 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  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.

  • Recent Advances in Quinoline-Based Macrocycles: Synthesis, Properties, and Applications in Catalytic Reactions

    Xu W., Kumagai N.

    Synthesis (Germany) 56 ( 11 ) 1765 - 1774 2024.05

    Research paper (scientific journal), Last author, Corresponding author, Accepted,  ISSN  00397881

    　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 various applicable fields, such as chemistry, materials science, and biology. Crown ethers, calixarenes, and porphyrinoids, which contain several ether/phenol/pyrrole subunits, represent these molecular categories with unparalleled functional diversity. In contrast, quinoline-based macrocycles comprising the quinoline unit as a key element to construct specific ring shapes have received limited attention. In this minireview, we summarize the recent advances in oligoquinoline macrocycles TriQuinoline (TQ), oxa-TriQuinoline (o-TQ), TEtraQuinoline (TEQ), and other bridged quinoline-based macrocycles. 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 quinoline-based macrocycle family. 1 Introduction 2 Quinoline-Based Macrocycles 2.1 TriQuinoline (TQ) 2.2 Oxa-TriQuinoline (o-TQ) 2.3 TEtraQuinoline (TEQ) 2.4 Larger Quinoline-Based Macrocycles with Bridges 3 Conclusion.

  • In2Q2: A New Entry of 16-Membered Tetraazamacrocycle Concatenating Indole and Quinoline Units

    Kihara K., Kobayashi T., Xu W., Kumagai N.

    Chemistry - A European Journal 30 ( 25 )  2024.05

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

    　View Summary

    A new family of 16-membered macrocycles comprising two indole (In) and two quinoline (Q) units, coined In2Q2, was synthesized. Each unit is diagonally located and concatenated in a head-to-tail fashion, furnishing a non-flat saddle-shaped architecture with C2 symmetry. The synthetic protocol utilizing macrocyclic diamide as a pivotal precursor allowed us to access a series of In2Q2 derivatives bearing various substituents on the periphery. The In2Q2 derivatives and their Zn2+ complexes were emissive in both solution phase and solid state. While the entire architecture of In2Q2 is similar to that of quinoline tetramer TEtraQuinoline, a couple of contrasting physicochemical properties were revealed.

  • Chemoselective Catalytic Dehydrogenation of Benzylic Amines Driven by the TEtraQuinoline/FeCl<inf>2</inf> Complex

    Nishiwaki M., Xu W., Kumagai N.

    Asian Journal of Organic Chemistry (Asian Journal of Organic Chemistry)  12 ( 9 )  2023.09

    Last author, Corresponding author, Accepted,  ISSN  21935807

    　View Summary

    A chemoselective dehydrogenation protocol for benzylic amines catalyzed by the TEtraQuinoline (TEQ)/FeCl2 complex is described. In combination with 2 equiv of tert-butyl hydroperoxide, as little as 0.1 mol% of catalyst loading was sufficient to convert primary and secondary benzylic amines to the corresponding imines and dimerized imines, respectively. Subsequent hydrolysis of the imines allowed for removal of the benzyl group on the nitrogen atom. Nonaromatic carbon-carbon multiple bonds and the O-Bn group remained intact in the present protocol, providing a complementary deprotection procedure to reductive removal conditions exerted by Pd catalysis.

  • Oxa-TriQuinoline: A New Entry to Aza-Oxa-Crown Architectures**

    Kobayashi T., Kumagai N.

    Angewandte Chemie - International Edition (Angewandte Chemie - International Edition)  62 ( 32 )  2023.08

    Research paper (scientific journal), Last author, Corresponding author, Accepted,  ISSN  14337851

    　View Summary

    A new 15-membered-macrocyclic molecular entity, oxa-TriQuinoline (o-TQ), was designed and synthesized. In o-TQ, three oxygen atoms were joined onto three quinoline units at the 2- and 8-positions in a head-to-tail fashion by three-fold SNAr reactions, giving rise to the characteristic N3O3 aza-oxa-crown architecture. o-TQ can serve as a new tridentate nitrogen ligand to capture a CuI cation and adopt a bowl shape, before supramolecular complexation with corannulene and [12]cycloparaphenylene (CPP) occurs through π–π and CH–π interactions. In the presence of the CuI cation, the non-emissive o-TQ becomes a highly emissive material in the solid state, whereby the emission wavelengths depend on the ancillary ligand on the CuI cation. The o-TQ/CuI complex is able to promote carbene catalysis to provide a range of enamines with a gem-difluorinated terminus.

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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

    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

    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

    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

    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

    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

  • Diversification of Molecular Functions via Unique Molecular Design

    2023.04
    -
    2026.03

    基盤研究(B), 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

  • Porphyrin 2.0: Chemistry of Warped-Porphyrin

    2022.06
    -
    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 】

  • DRUG SYNTHESIS LABORATORY COURSE

    2025

  • DRUG SYNTHESIS AND PROCESS CHEMISTRY

    2025

  • CHEMISTRY OF BIOACTIVE SUBSTANCES

    2025

  • BIOORGANIC CHEMISTRY: STRUCTURE AND CHEMISTRY OF BIOMOLECULES

    2025

  • BIOORGANIC CHEMISTRY: REACTION OF BIOMOLECULES

    2025

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