Updated on 2021/05/25

写真a

 
MASUI Hisashi
 
Organization
Graduate School of Pharmaceutical Sciences Department of Basic Medicinal Sciences Organic Chemistry Assistant Professor
Graduate School
Graduate School of Pharmaceutical Sciences
Title
Assistant Professor
External link

Degree 1

  1. 博士(工学) ( 2013.3   東京工業大学 ) 

 

Papers 13

  1. Efficient synthesis of 5-(hydroxymethyl)piperazin-2-ones using automatically prepared chiral bromocarboxylic acid and Garner's aldehyde as versatile building blocks.

    Masui H, Naito K, Minoshima M, Kusayanagi A, Yosugi S, Shoji M, Takahashi T

    Bioorganic & medicinal chemistry letters   Vol. 40   page: 127961   2021.3

  2. Solution-phase automated synthesis of an alpha-amino aldehyde as a versatile intermediate Reviewed

    Hisashi Masui, Sae Yosugi, Shinichiro Fuse, Takashi Takahashi

    BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY   Vol. 13   page: 106 - 110   2017

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    Language:English   Publishing type:Research paper (scientific journal)   Publisher:BEILSTEIN-INSTITUT  

    A solution-phase automated synthesis of the versatile synthetic intermediate, Garner's aldehyde, was demonstrated. tert-Butoxycarbonyl (Boc) protection, acetal formation, and reduction of the ester to the corresponding aldehyde were performed utilizing our originally developed automated synthesizer, ChemKonzert. The developed procedure was also useful for the synthesis of Garner's aldehyde analogues possessing fluorenylmethyloxycarbonyl (Fmoc) or benzyloxycarbonyl (Cbz) protection.

    DOI: 10.3762/bjoc.13.13

    Web of Science

    PubMed

  3. One-pot, three-component coupling approach to the synthesis of α-iminocarboxamides Reviewed

    Hisashi Masui, Shinichiro Fuse, Takashi Takahashi

    Organic Letters   Vol. 14 ( 16 ) page: 4090-4093   2012

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    Authorship:Lead author   Language:English   Publishing type:Research paper (scientific journal)  

    DOI: 10.1021/ol3017337

  4. Rapid and Mild Lactamization Using Highly Electrophilic Triphosgene in a Microflow Reactor

    Fuse Shinichiro, Komuro Keiji, Otake Yuma, Masui Hisashi, Nakamura Hiroyuki

    CHEMISTRY-A EUROPEAN JOURNAL     2021.3

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    Publisher:Chemistry - A European Journal  

    DOI: 10.1002/chem.202100059

    Web of Science

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  5. Unique responses of Helicobacter pylori to exogenous hydrophobic compounds.

    Shimomura H, Wanibuchi K, Hosoda K, Amgalanbaatar A, Masui H, Takahashi T, Hirai Y

    Chemistry and physics of lipids   Vol. 229   page: 104908   2020.7

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    Language:English   Publishing type:Research paper (scientific journal)  

    DOI: 10.1016/j.chemphyslip.2020.104908

    PubMed

  6. Antibacterial effect of indene on Helicobacter pylori correlates with specific interaction between its compound and dimyristoyl-phosphatidylethanolamine.

    Wanibuchi K, Takezawa M, Hosoda K, Amgalanbaatar A, Tajiri K, Koizumi Y, Niitsu S, Masui H, Sakai Y, Shoji M, Takahashi T, Hirai Y, Shimomura H

    Chemistry and physics of lipids   Vol. 227   page: 104871   2020.3

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    Language:English   Publishing type:Research paper (scientific journal)  

    DOI: 10.1016/j.chemphyslip.2020.104871

    PubMed

  7. Donor-acceptor polymers containing thiazole-fused benzothiadiazole acceptor units for organic solar cells Reviewed

    Nakamura Tomoya, Ishikura Yasuhisa, Arakawa Noriko, Hori Megumi, Satou Motoi, Endo Masaru, Masui Hisashi, Fuse Shinichiro, Takahashi Takashi, Murata Yasujiro, Murdey Richard, Wakamiya Atsushi

    RSC ADVANCES   Vol. 9 ( 13 ) page: 7107 - 7114   2019

  8. Indene Compounds Synthetically Derived from Vitamin D Have Selective Antibacterial Action on Helicobacter pylori Reviewed

    Kiyofumi Wanibuchi, Kouichi Hosoda, Masato Ihara, Kentaro Tajiri, Yuki Sakai, Hisashi Masui, Takashi Takahashi, Yoshikazu Hirai, Hirofumi Shimomura

    Lipids   Vol. 53 ( 4 ) page: 393 - 401   2018.4

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    Language:English   Publishing type:Research paper (scientific journal)   Publisher:John Wiley and Sons Inc.  

    Helicobacter pylori infects the human stomach and is closely linked with the development of gastric cancer. When detected, this pathogen can be eradicated from the human stomach using wide-spectrum antibiotics. However, year by year, H. pylori strains resistant to the antibacterial action of antibiotics have been increasing. The development of new antibacterial substances effective against drug-resistant H. pylori is urgently required. Our group has recently identified extremely selective bactericidal effects against H. pylori in (1R,3aR,7aR)-1-[(1R)-1,5-dimethylhexyl]octahydro-7a-methyl-4H-inden-4-one (VDP1) (otherwise known as Grundmann's ketone), an indene compound derived from the decomposition of vitamin D3 and proposed the antibacterial mechanism whereby VDP1 induces the bacteriolysis by interacting at least with PtdEtn (dimyristoyl-phosphatidylethanolamine [di-14:0 PtdEtn]) retaining two 14:0 fatty acids of the membrane lipid constituents. In this study, we synthesized new indene compounds ((1R,3aR,7aR)-1-((2R,E)-5,6-dimethylhept-3-en-2-yl)-7a-methyloctahydro-4H-inden-4-one [VD2-1], (1R,3aR,7aR)-1-((S)-1-hydroxypropan-2-yl)-7a-methyloctahydro-1H-inden-4-ol [VD2-2], and (1R,3aR,7aR)-7a-methyl-1-((R)-6-methylheptan-2-yl)octahydro-1H-inden-4-ol [VD3-1]) using either vitamin D2 or vitamin D3 as materials. VD2-1 and VD3-1 selectively disrupted the di-14:0 PtdEtn vesicles without destructing the vesicles of PtdEtn (dipalmitoyl-phosphatidylethanolamine) retaining two 16:0 fatty acids. In contrast, VD2-2, an indene compound lacking an alkyl group, had no influence on the structural stability of both PtdEtn vesicles. In addition, VD2-1 and VD3-1 exerted extremely selective bactericidal action against H. pylori without affecting the viability of commonplace bacteria. Meanwhile, VD2-2 almost forfeited the bactericidal effects on H. pylori. These results suggest that the alkyl group of the indene compounds has a crucial conformation to interact with di-14:0 PtdEtn of H. pylori membrane lipid constituents whereby the bacteriolysis is ultimately induced.

    DOI: 10.1002/lipd.12043

    Web of Science

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  9. Identification and characterization of a novel NADPH oxidase 1 (Nox1) inhibitor that suppresses proliferation of colon and stomach cancer cells Reviewed

    Tsuyoshi Yamamoto, Hirofumi Nakano, Kazuro Shiomi, Kiyofumi Wanibuchi, Hisashi Masui, Takashi Takahashi, Yasuteru Urano, Tohru Kamata

    Biological and Pharmaceutical Bulletin   Vol. 41 ( 3 ) page: 419 - 426   2018.3

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    Language:English   Publishing type:Research paper (scientific journal)   Publisher:Pharmaceutical Society of Japan  

    Reactive oxygen species (ROS) generated by reduced nicotinamide adenine dinucleotide phosphate (NADPH) oxidase (Nox)1 mediate cellular signalings involved in normal physiological processes, and aberrant control of Nox1 has been implicated in the pathogenesis of various diseases. Therefore, Nox1 could have great potential as a therapeutic target. Here, we identified a novel Nox1 inhibitor, NOS31 secreted from Stretomyces sp. and analyzed its chemical structure. Furthermore, NOS31 was found to selectively inhibit Nox1-mediated ROS generation, with only a marginal effect on other Nox isoforms (Nox2–5) and no ROS scavenging activity. This compound blocked both Nox organizer 1 (NOXO1)/Nox activator 1 (NOXA1)-depen-dent and phorbol 12-myristate 13-acetate-stimulated Nox1-mediated ROS production in colon cancer cells. NOS31 inhibited the proliferation of several colon carcinoma and gastric cancer cell lines that upregulate the Nox1 system, whereas it had no appreciable effect on normal cells with low levels of Nox1. The finding suggests that NOS31 is a unique, potent Nox1 inhibitor of microbial origin and raises its possibility as a therapeutic agent for inhibiting gastrointestinal cancer cell growth.

    DOI: 10.1248/bpb.b17-00804

    Web of Science

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  10. D–π–A Dyes that Contain New Hydantoin Anchoring Groups for Dye-Sensitized Solar Cells Reviewed

    Hisashi Masui, Masato M. Maitani, Shinichiro Fuse, Ayaka Yamamura, Yuhei Ogomi, Shuzi Hayase, Tatsuo Kaiho, Hiroshi Tanaka, Yuji Wada, Takashi Takahashi

    Asian Journal of Organic Chemistry   Vol. 7 ( 2 ) page: 458 - 464   2018.2

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    Language:English   Publishing type:Research paper (scientific journal)   Publisher:Wiley-VCH Verlag  

    The development of new anchoring groups is important to facilitate effective co-sensitization in dye-sensitized solar cells (DSSCs). Herein, stable organic D–π–A dyes that contain new heterocyclic hydantoin-based anchoring groups have been designed, synthesized, and used in DSSCs. These dye sensitizers were evaluated in terms of their absorption spectra, electrochemical properties, and performance in DSSC devices. Although only one-third of the amount of hydantoin-containing dyes adsorbed onto TiO2 relative to their cyanoacrylic-acid-containing analogues, they exhibited effective photoexcited electron-transfer properties. External quantum efficiencies of over 80 % was observed, which were comparable to those of the cyanoacrylic-acid-containing dyes. In addition, the new hydantoin-containing dyes exhibited significant robustness, which could allow improved stability of their corresponding photovoltaic devices under harsh conditions, such as high temperature and humidity.

    DOI: 10.1002/ajoc.201700542

    Web of Science

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  11. One-pot, diversity-oriented synthesis of aryl-substituted benzoxacycles including benzofuran, coumarin, and benzoxazepine Reviewed

    Hisashi Masui, Eri Ohkawa, Rika Kitahara, Kiyofumi Wanibuchi, Takashi Takahashi

    Heterocycles   Vol. 94 ( 12 ) page: 2273 - 2290   2017

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    Language:English   Publishing type:Research paper (scientific journal)   Publisher:Japan Institute of Heterocyclic Chemistry  

    A one-pot method for the synthesis of benzoxacycles including benzofuran, coumarin, benzoxazepine, and benzoxazocine from a common synthetic intermediate was established. Benzoxacycles are privileged structures in medicinal chemistry and have featured in several clinically used drugs. The synthesis of a benzofuran containing an aryl substituent was accomplished using potassium carbonate and sodium hydride. The one-pot synthesis of coumarin was also carried out using trans-decalin as the solvent. The optimized conditions for the one-pot synthesis of benzoxazepine can also be applied to the synthesis of benzoxazocine.

    DOI: 10.3987/COM-17-13791

    Web of Science

    Scopus

  12. Total Synthesis of (+)-Antimycin A3b on Solid Supports Reviewed

    Yusuke Iijima, Osamu Kimata, Santida Decharin, Hisashi Masui, Yoichiro Hirose, Takashi Takahashi

    European Journal of Organic Chemistry   Vol. 2014 ( 22 ) page: 4725-4732   2014

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    Language:English   Publishing type:Research paper (scientific journal)  

    DOI: 10.1002/ejoc.201402430

  13. Combinatorial synthesis and evaluation of α-iminocarboxamide-nickel (II) catalysts for the copolymerization of ethylene and a polar monomer Reviewed

    Shinichiro Fuse, Hisashi Masui, Akio Tannna, Fumihiko Shimizu, Takashi Takahashi

    ACS Combinatorial Science   Vol. 14 ( 1 ) page: 17-24   2012

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    Language:English   Publishing type:Research paper (scientific journal)  

    DOI: 10.1021/co200081j

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MISC 12

  1. ベンゾフランをプラットフォームとしたπ‐共役化合物ライブラリーの構築

    増井悠, 鹿倉彩乃, 鰐渕清史, 庄司満, 高橋孝志

    日本薬学会年会要旨集(CD-ROM)   Vol. 139th   page: ROMBUNNO.22PO‐am051   2019

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    Language:Japanese  

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  2. ヒドロホルミル化反応のフローへの適応と合成への応用

    増井悠, 新津さくら, 本田瑛樹, 庄司満, 高橋孝志

    日本薬学会年会要旨集(CD-ROM)   Vol. 139th   page: ROMBUNNO.21PO‐am026   2019

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  3. コンビナトリアルライブラリーの構築を指向したエバーメクチン類の全合成研究

    齋藤亮, 君嶋葵, 君嶋葵, 千成恒, 佐藤翔悟, 廣瀬友靖, 廣瀬友靖, 増井悠, 高橋孝志, 大村智, 砂塚敏明, 砂塚敏明

    日本薬学会年会要旨集(CD-ROM)   Vol. 139th   page: ROMBUNNO.21PO‐pm009S   2019

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  4. マイクロフローリアクターを活用した安全かつ効率的ヒドロホルミル化反応の開発

    増井悠

    旭硝子財団研究助成成果発表会   Vol. 2018   page: 44‐45   2018.7

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    Language:Japanese  

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  5. Development of safe and efficient hydroformylation using flow reactor

    増井 悠

    旭硝子財団助成研究成果報告 Reports of research assisted by the Asahi Glass Foundation     page: 1 - 8   2018

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    Language:Japanese   Publisher:旭硝子財団  

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  6. ペプチドミメティックスとしての活用を指向したケトピペラジンのライブラリー合成

    増井悠, 美濃島麻衣, 庄司満, 高橋孝志

    日本薬学会年会要旨集(CD-ROM)   Vol. 138th   page: ROMBUNNO.27PA‐pm024   2018

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  7. 3Dプリンターで自作したフロー反応器で医薬品原料を合成する

    増井 悠

    ファルマシア   Vol. 54 ( 1 ) page: 68 - 68   2018

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    Language:Japanese   Publisher:公益社団法人 日本薬学会  

    フロー反応は,管内に試薬を流通させながら化学反応を行う手法であり,フラスコなどを用いるバッチ反応と比較して安全性,生産性に優れている.また,従来のフラスコ内でのかく拌とは異なり,微小空間において試薬を衝突させて混合を行うため,反応効率が向上することが知られている.一方で,反応の収率や選択性は反応器の形状(反応管の長さ,径,屈折など)に大きく依存するため,反応器の最適化が必要になり,簡便かつ目的に応じて反応器を微調整する工夫が必要である.3Dプリンターは,用途に合わせて迅速かつ自由自在に立体を造形でき,複雑な流路で構成されるフロー反応器の最適化において極めて効果的である.今回PuglisiとBenagliaらは,3Dプリンターで自作したフロー反応器を用い,医薬品原料として多用される光学活性1,2-アミノアルコール1の不斉合成に成功したので,本稿にて紹介する.<br>なお,本稿は下記の文献に基づいて,その研究成果を紹介するものである.<br>1) Movsisyan M. <i>et</i> <i>al</i>., <i>Chem</i>. <i>Soc</i>. <i>Rev</i>., <b>45</b>, 4892-4928(2016).<br>2) Rossi S. <i>et</i> <i>al</i>., <i>Angew</i>. <i>Chem</i>. <i>Int</i>. <i>Ed</i>., <b>56</b>, 4290-4294(2017).

    CiNii Article

  8. α‐ケトカルボン酸類縁体の簡便な合成法の開発とそのヘテロ環合成への応用

    増井悠, DECHARIN Santida, 布施新一郎, 高橋孝志

    日本薬学会年会要旨集(CD-ROM)   Vol. 138th   page: ROMBUNNO.26M‐am04   2018

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  9. 新規創薬テンプレートとしての活用を指向したジアザビシクロノナン類縁体とケトピペラジン類縁体の合成

    増井悠, 荻江泰成, 高橋孝志

    日本薬学会年会要旨集(CD-ROM)   Vol. 137th   page: ROMBUNNO.25PA‐am098   2017

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  10. ペプチドミメティクスとしての応用を指向したケトピペラジン類縁体の自動合成法の開発

    増井悠, 草柳彰, 高橋孝志

    日本薬学会年会要旨集(CD-ROM)   Vol. 137th   page: ROMBUNNO.25PA‐am097   2017

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  11. フローリアクターを用いた安全なヒドロホルミル化法の開発

    増井悠, 本田瑛樹, 高橋孝志

    日本薬学会年会要旨集(CD-ROM)   Vol. 137th   page: ROMBUNNO.26S‐pm02   2017

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  12. コンビナトリアルライブラリーの構築を指向したエバーメクチン類の全合成研究;ファーマコフォアフラグメントの合成

    千成恒, 千成恒, 廣瀬友靖, 廣瀬友靖, 増井悠, 高橋孝志, 大村智, 砂塚敏明, 砂塚敏明

    日本薬学会年会要旨集(CD-ROM)   Vol. 137th   page: ROMBUNNO.27S‐am02S   2017

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KAKENHI (Grants-in-Aid for Scientific Research) 3

  1. Biomimetic synthesis of pyrrolizidine alkaloid based on structurally diversity-oriented aproach

    Grant number:20K15462  2020.4 - 2022.3

    Grant-in-Aid for Early-Career Scientists

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    Authorship:Principal investigator 

    Grant amount:\4160000 ( Direct Cost: \3200000 、 Indirect Cost:\960000 )

  2. Biomimetic synthesis of amino acid using continuous flow reactor packed with reagents/catalysts

    Grant number:18K14401  2018.4 - 2020.3

    Grant-in-Aid for Early-Career Scientists

    Masui Hisashi

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    Authorship:Principal investigator 

    Grant amount:\4160000 ( Direct Cost: \3200000 、 Indirect Cost:\960000 )

    The purpose of this study is to synthesize amino acids from carbon dioxide biomimetically. α-Ketocarboxylic acid is synthesized from carbon dioxide and aldehyde (carbon fixation) using thiamine analogues as a catalyst, and then α-ketocarboxylic acid is converted to an amino acid (transamination).
    In carbon fixation, we prepared a complex of aldehyde and thiamine analogues preliminary and examined the addition of this complex to isocyanate. As a result, it was found that α-ketocarboxamide was obtained sufficiently when the reaction was carried out with a combination of triethylamine-acetonitrile. Using this condition, the reaction proceeded even when carbon dioxide was used, and the target α-ketocarboxylic acid was obtained.

  3. Synthesis of an Antibacterial Compound for Helicobacter pylori

    Grant number:15K08006  2015.4 - 2018.3

    kiyofumi wanibuchi

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    Authorship:Coinvestigator(s) 

    VDP1 is a selective antibacterial compound that targets Helicobacter pylori and does not act on other typical bacteria. Herein, we provide a straightforward and mild one-pot method for the synthesis of VDP1 from vitamin D3. The yield of VDP1 synthesized by the ruthenium-periodate oxidization of the compound generated from the aza-Diels-Alder reaction of vitamin D3 and 4-phenyl-1,2,4-triazoline-3,5-dione was greater than that produced via direct ruthenium-periodate catalytic oxidation of vitamin D3.

Industrial property rights 1

  1. 色素増感型光電変換素子用のヘテロ環リンカー基を有する完全有機色素化合物、およびそれを用いた光電変換素子

    高橋 孝志, 増井 悠, 布施 新一郎, 海宝 龍夫, 和田 雄二, 米谷 真人, 早瀬 修二, 尾込 裕平

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    Applicant:関東天然瓦斯開発株式会社, 学校法人都築第一学園, 国立大学法人東京工業大学, 国立大学法人九州工業大学

    Application no:特願2015-201952  Date applied:2015.10

    Announcement no:特開2017-076648  Date announced:2017.4

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