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Synthetic studies of alkaloids possessing iNOS inducing activities

Research Project

Project/Area Number 18K06558
Research Category

Grant-in-Aid for Scientific Research (C)

Allocation TypeMulti-year Fund
Section一般
Review Section Basic Section 47010:Pharmaceutical chemistry and drug development sciences-related
Research InstitutionToho University

Principal Investigator

TAKAHASHI Keisuke  東邦大学, 薬学部, 准教授 (60380854)

Co-Investigator(Kenkyū-buntansha) 加藤 恵介  東邦大学, 薬学部, 教授 (80276609)
Project Period (FY) 2018-04-01 – 2021-03-31
Project Status Completed (Fiscal Year 2020)
Budget Amount *help
¥4,290,000 (Direct Cost: ¥3,300,000、Indirect Cost: ¥990,000)
Fiscal Year 2020: ¥1,170,000 (Direct Cost: ¥900,000、Indirect Cost: ¥270,000)
Fiscal Year 2019: ¥1,560,000 (Direct Cost: ¥1,200,000、Indirect Cost: ¥360,000)
Fiscal Year 2018: ¥1,560,000 (Direct Cost: ¥1,200,000、Indirect Cost: ¥360,000)
Keywords全合成 / 天然物 / アルカロイド / iNOS / ウルポシジン / NO / 一酸化窒素
Outline of Final Research Achievements

Synthesis of urupocidin A was examined. The left segment of urupocidine A was synthesized stereoselectively starting from 4-octynoic acid via coupling with the acetylide, asymmetric reduction, trans reduction, epoxidation, reduction of the epoxide and oxidation. The lactone intermediate possessing the framework and asymmetric centers of the left segment was obtained. On the other hand, the right segment was synthesized via Keck asymmetric allylation, mesylation and Gabriel syntheses.

Academic Significance and Societal Importance of the Research Achievements

最近単離構造決定され医薬品リード化合物として期待されるウルポシジンAをとり上げ、これらの独自の方法論に基づく初の全合成達成を本研究の目的と定め研究を展開した。その結果、今後の展開に重要と思われる左右両フラグメントを合成することができ、本研究によりウルポシジン及びその誘導体の化学合成を可能とする端緒を見いだすことができた。

Report

(4 results)
  • 2020 Annual Research Report   Final Research Report ( PDF )
  • 2019 Research-status Report
  • 2018 Research-status Report
  • Research Products

    (15 results)

All 2021 2020 2019 2018

All Journal Article (7 results) (of which Int'l Joint Research: 1 results,  Peer Reviewed: 6 results,  Open Access: 2 results) Presentation (8 results)

  • [Journal Article] Aging-related changes in the sensitivity of behavioral effects of the neonicotinoid pesticide clothianidin in male mice2021

    • Author(s)
      Hirano Tetsushi、Miyata Yuka、Kubo Shizuka、Ohno Shuji、Onaru Kanoko、Maeda Mizuki、Kitauchi Sayaka、Nishi Misaki、Tabuchi Yoshiaki、Ikenaka Yoshinori、Ichise Takahiro、Nakayama Shouta M.M.、Ishizuka Mayumi、Arizono Koji、Takahashi Keisuke、Kato Keisuke、Mantani Youhei、Yokoyama Toshifumi、Hoshi Nobuhiko
    • Journal Title

      Toxicology Letters

      Volume: 342 Pages: 95-103

    • DOI

      10.1016/j.toxlet.2021.02.010

    • Related Report
      2020 Annual Research Report
    • Peer Reviewed / Open Access
  • [Journal Article] Interspecies differences in cytochrome P450-mediated metabolism of neonicotinoids among cats, dogs, rats, and humans2021

    • Author(s)
      Khidkhan Kraisiri、Ikenaka Yoshinori、Ichise Takahiro、Nakayama Shouta M.M.、Mizukawa Hazuki、Nomiyama Kei、Iwata Hisato、Arizono Koji、Takahashi Keisuke、Kato Keisuke、Ishizuka Mayumi
    • Journal Title

      Comparative Biochemistry and Physiology Part C: Toxicology & Pharmacology

      Volume: 239 Pages: 108898-108898

    • DOI

      10.1016/j.cbpc.2020.108898

    • NAID

      120007181823

    • Related Report
      2020 Annual Research Report
    • Peer Reviewed / Int'l Joint Research
  • [Journal Article] Improved Synthesis and Determination of the Biologically Active Diastereomer of YK112020

    • Author(s)
      Kanno Yuichiro、Kusakabe Taichi、Saito Nao、Kikkawa Shoko、Takahashi Keisuke、Azumaya Isao、Nemoto Kiyomitsu、Kato Keisuke
    • Journal Title

      Molbank

      Volume: 2020 Issue: 2 Pages: M1125-M1125

    • DOI

      10.3390/m1125

    • Related Report
      2020 Annual Research Report
    • Peer Reviewed / Open Access
  • [Journal Article] Total Synthesis of (?)-Graminin A Based on Asymmetric Cyclization Carbonylation of Propargyl Acetate2019

    • Author(s)
      Ito Yoichi、Kusakabe Taichi、Dhage Yogesh Daulat、Takahashi Keisuke、Sakata Ken、Sasai Hiroaki、Kato Keisuke
    • Journal Title

      The Journal of Organic Chemistry

      Volume: 84 Issue: 24 Pages: 16268-16277

    • DOI

      10.1021/acs.joc.9b02886

    • Related Report
      2019 Research-status Report
    • Peer Reviewed
  • [Journal Article] PdII catalyzed ligand controlled synthesis of bis(3-furanyl)methanones and methyl 3-furancarboxylates2019

    • Author(s)
      Kusakabe Taichi、Mochida Tomoyuki、Ariyama Tomohiro、Lee Dong、Ohkubo Shin、Takahashi Keisuke、Kato Keisuke
    • Journal Title

      Organic & Biomolecular Chemistry

      Volume: 17 Issue: 28 Pages: 6860-6865

    • DOI

      10.1039/c9ob01189g

    • Related Report
      2019 Research-status Report
    • Peer Reviewed
  • [Journal Article] Syntheses of 4‐OH and 5‐OH Imidacloprids2019

    • Author(s)
      Takahashi Keisuke、Tsurumi Tatsuya、Inami Moe、Li Zui、Kusakabe Taichi、Kikkawa Shoko、Azumaya Isao、Tominaga Nobuaki、Ikenaka Yoshinori、Arizono Koji、Kato Keisuke
    • Journal Title

      ChemistrySelect

      Volume: 4 Issue: 24 Pages: 7343-7345

    • DOI

      10.1002/slct.201901491

    • Related Report
      2019 Research-status Report
    • Peer Reviewed
  • [Journal Article] Asymmetric Cyclizative Dimerization of ( ortho ‐Alkynyl Phenyl) (Methoxymethyl) Sulfides with Palladium(II) Bisoxazoline Catalyst2018

    • Author(s)
      Peng Cheng、Kusakabe Taichi、Kikkawa Shoko、Mochida Tomoyuki、Azumaya Isao、Dhage Yogesh Daulat、Takahashi Keisuke、Sasai Hiroaki、Kato Keisuke
    • Journal Title

      Chemistry A European Journal

      Volume: 25 Issue: 3 Pages: 733-737

    • DOI

      10.1002/chem.201804779

    • Related Report
      2018 Research-status Report
  • [Presentation] Urupocidin A の合成研究2021

    • Author(s)
      高橋 圭介、塚本 拓也、仙田 桂子、冨山 海渡、福井 沙耶香、吉田 佳奈、日下部 太一、加藤 恵介
    • Organizer
      日本薬学会第141年会
    • Related Report
      2020 Annual Research Report
  • [Presentation] パラジウム触媒を用いた末端アレンの不斉メトキシ-カルボニル化反応の開発2021

    • Author(s)
      日下部 太一、守 朱音、吉若 健太郎、水島 康太、赤田 彗太、高橋 圭介、笹井 宏明、加藤 恵介
    • Organizer
      日本薬学会第141年会
    • Related Report
      2020 Annual Research Report
  • [Presentation] Urupocidin A の合成研究2020

    • Author(s)
      高橋圭介
    • Organizer
      日本薬学会第140年会
    • Related Report
      2019 Research-status Report
  • [Presentation] Box-Pd(II)錯体による交差CCC-Coupling反応2019

    • Author(s)
      加藤 恵介
    • Organizer
      日本薬学会第139年会
    • Related Report
      2018 Research-status Report
  • [Presentation] ネオニコチノイド系農薬代謝物の合成2019

    • Author(s)
      高橋圭介
    • Organizer
      日本薬学会第139年会
    • Related Report
      2018 Research-status Report
  • [Presentation] アレンのパラジウム触媒的不斉メトキシ-カルボニル化反応の開発2019

    • Author(s)
      日下部太一
    • Organizer
      日本薬学会第139年会
    • Related Report
      2018 Research-status Report
  • [Presentation] プロパルギルアセテートの不斉環化-カルボニル化を基盤としたグラミニン A の全合成2018

    • Author(s)
      伊藤陽一
    • Organizer
      第48回複素環化学討論会
    • Related Report
      2018 Research-status Report
  • [Presentation] Mohangic acids の合成研究2018

    • Author(s)
      高橋圭介
    • Organizer
      第48回複素環化学討論会
    • Related Report
      2018 Research-status Report

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Published: 2018-04-23   Modified: 2022-01-27  

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