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Development of novel anti-virus drugs by means of libraries of sialic acid derivatives possessing an anion at the 1-position

Research Project

Project/Area Number 25350976
Research Category

Grant-in-Aid for Scientific Research (C)

Allocation TypeMulti-year Fund
Section一般
Research Field Chemical biology
Research InstitutionUniversity of Toyama

Principal Investigator

CHIBA Junya  富山大学, 大学院医学薬学研究部(薬学), 助教 (50436789)

Co-Investigator(Renkei-kenkyūsha) HATANAKA Yasumaru  富山大学, 事務局, 理事・副学長 (30111181)
TOMOHIRO Takenori  富山大学, 大学院医学薬学研究部(薬学), 准教授 (70357581)
Project Period (FY) 2013-04-01 – 2017-03-31
Project Status Completed (Fiscal Year 2016)
Budget Amount *help
¥4,940,000 (Direct Cost: ¥3,800,000、Indirect Cost: ¥1,140,000)
Fiscal Year 2015: ¥1,690,000 (Direct Cost: ¥1,300,000、Indirect Cost: ¥390,000)
Fiscal Year 2014: ¥1,690,000 (Direct Cost: ¥1,300,000、Indirect Cost: ¥390,000)
Fiscal Year 2013: ¥1,560,000 (Direct Cost: ¥1,200,000、Indirect Cost: ¥360,000)
Keywords医薬品探索 / シアル酸誘導体 / クリックケミストリー / アシルスルホンアミド / スルホニルアミジン / ノイラミニダーゼ / 阻害剤 / 抗インフルエンザ / シアル酸 / スルホクリック / チオアミドクリック / アニオン / スルホクリック反応 / スルホニルアジド / チオアミド
Outline of Final Research Achievements

In this study, we developed novel candidates of anti-flu medicine. We originally designed them based on the plus and minus charge in the zanamivir and derivatized them effictiently by means of click chemistry. The candidate inhibitors showed high inhibitory ability to neuraminidase comparable to that of zanamivir. In addition, they also exhibited high affinity to the mutant neuraminidase with oseltamivir resistant. We applied 3 patents, got 1 patent, had 17 presentations, reported 3 original articles, and published 1 book in regard to the results in this study.

Report

(5 results)
  • 2016 Annual Research Report   Final Research Report ( PDF )
  • 2015 Research-status Report
  • 2014 Research-status Report
  • 2013 Research-status Report
  • Research Products

    (27 results)

All 2016 2015 2014 2013 Other

All Journal Article (2 results) (of which Peer Reviewed: 2 results,  Acknowledgement Compliant: 1 results) Presentation (17 results) (of which Int'l Joint Research: 3 results) Book (1 results) Remarks (2 results) Patent(Industrial Property Rights) (5 results)

  • [Journal Article] Evaluation of dipole moment and electrophilicity on the nature of click-type coupling reaction between thioamide and sulfonyl azide2016

    • Author(s)
      Muhammad Aswad, Junya Chiba,* Takenori Tomohiro, Yasumaru Hatanaka*
    • Journal Title

      Tetrahedron Letters

      Volume: 57 Issue: 12 Pages: 1313-1316

    • DOI

      10.1016/j.tetlet.2016.02.028

    • Related Report
      2015 Research-status Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Coupling reaction of thioamides with sulfonyl azides : An efficient catalyst-free click-type ligation under mild conditions2013

    • Author(s)
      Muhammad Aswad, Junya Chiba, Takenori Tomohiro and Yasumaru Hatanaka
    • Journal Title

      Chem. Commun

      Volume: 49 Issue: 87 Pages: 10242-10244

    • DOI

      10.1039/c3cc46055j

    • Related Report
      2013 Research-status Report
    • Peer Reviewed
  • [Presentation] 触媒不要の新規なクリック型の化学反応に用いる試薬類2016

    • Author(s)
      千葉順哉
    • Organizer
      Toyama Science GALA 2016
    • Place of Presentation
      富山市
    • Year and Date
      2016-09-30
    • Related Report
      2016 Annual Research Report
  • [Presentation] Novel Click-type Coupling Reaction of Thioamides with Sulfonyl Azides: Scope, Mechanism and Application2016

    • Author(s)
      Muhammad Aswad, Junya Chiba, Yasumaru Hatanaka, Takenori Tomohiro
    • Organizer
      The First International Symposium on Toyama-Asia-Africa Phamaceutical Network
    • Place of Presentation
      Toyama
    • Year and Date
      2016-09-12
    • Related Report
      2016 Annual Research Report
    • Int'l Joint Research
  • [Presentation] A novel coupling reaction between thioamides and sulfonyl azides2016

    • Author(s)
      Kyoko Yamamoto, Muhammad Aswad, Junya Chiba, Yasumaru Hatanaka, Takenori Tomohiro
    • Organizer
      The First International Symposium on Toyama-Asia-Africa Phamaceutical Network
    • Place of Presentation
      Toyama
    • Year and Date
      2016-09-12
    • Related Report
      2016 Annual Research Report
    • Int'l Joint Research
  • [Presentation] チオアミドとスルホニルアジドのクリック型反応を利用したノイラミニダーゼ阻害剤の標的誘導型合成2016

    • Author(s)
      坂口 知美, 千葉 順哉, 中山 純, 畑中 保丸, 友廣 岳則
    • Organizer
      日本ケミカルバイオロジー学会 第11回年会
    • Place of Presentation
      京都市
    • Year and Date
      2016-06-15
    • Related Report
      2015 Research-status Report
  • [Presentation] チオアミドとスルホニルアジドを用いる新規クリック型反応2016

    • Author(s)
      山本 恭子, 千葉 順哉, Muhammad Aswad, 高橋 惇, 畑中 保丸, 友廣 岳則
    • Organizer
      日本薬学会第136年会
    • Place of Presentation
      横浜市
    • Year and Date
      2016-03-26
    • Related Report
      2015 Research-status Report
  • [Presentation] A click-type coupling reaction between thioamides and sulfonyl azides as a versatile approach to generate new pharmacologically active compounds2015

    • Author(s)
      Muhammad Aswad, Junya Chiba, Yasumaru Hatanaka, Takenori Tomohiro
    • Organizer
      The 2nd International Current Breakthrough (ICB)-Pharma Symposium 2015
    • Place of Presentation
      Solo (Indonesia)
    • Year and Date
      2015-10-31
    • Related Report
      2015 Research-status Report
    • Int'l Joint Research
  • [Presentation] ザナミビル C1 位カルボキシ基変換型の新規ノイラミニダーゼ阻害剤の開発2015

    • Author(s)
      千葉順哉、志村みさき、國安和仁、中山純、橋田まみ、鈴木千尋、畑中保丸、友廣岳則
    • Organizer
      第9回バイオ関連化学シンポジウム
    • Place of Presentation
      熊本市
    • Year and Date
      2015-09-10
    • Related Report
      2015 Research-status Report
  • [Presentation] 新規なクリック反応に用いる試薬類2015

    • Author(s)
      千葉順哉
    • Organizer
      イノベーションジャパン-2015 大学見本市
    • Place of Presentation
      江東区
    • Year and Date
      2015-08-27
    • Related Report
      2015 Research-status Report
  • [Presentation] ザナミビルC1位変換型の新規ノイラミニダーゼ阻害薬の開発2015

    • Author(s)
      志村みさき、千葉順哉、國安和仁、中山純、橋田まみ、鈴木千尋、畑中保丸、友廣岳則
    • Organizer
      日本ケミカルバイオロジー学会 第10回年会
    • Place of Presentation
      仙台市
    • Year and Date
      2015-06-10
    • Related Report
      2015 Research-status Report
  • [Presentation] ザナミビル C1 位誘導化によるノイラミニダーゼ阻害剤の探索2015

    • Author(s)
      志村みさき、千葉順哉、國安和仁、中山純、橋田まみ、鈴木千尋、畑中保丸、友廣岳則
    • Organizer
      フォーラム富山 創薬 第41回研究会
    • Place of Presentation
      富山市
    • Year and Date
      2015-05-28
    • Related Report
      2015 Research-status Report
  • [Presentation] ザナミビル C1 位カルボキシ基誘導化体のノイラミニダーゼ阻害能評価2015

    • Author(s)
      千葉 順哉, 中山 純, 橋田 まみ, 鈴木 千尋, 志村 みさき, 畑中 保丸, 友廣 岳則
    • Organizer
      日本薬学会 第135年会
    • Place of Presentation
      神戸市
    • Year and Date
      2015-03-25 – 2015-03-28
    • Related Report
      2014 Research-status Report
  • [Presentation] A Catalyst-Free Bio-Orthogonal Coupling Reaction of Thioamides and Sulfonyl Azides2014

    • Author(s)
      Junya Chiba, Muhammad Aswad, Takenori Tomohiro, Yasumaru Hatanaka
    • Organizer
      24th French-Japanese Symposium on Medicinal and Fine Chemistry (FJS 2014)
    • Place of Presentation
      Lyon (France)
    • Year and Date
      2014-09-14 – 2014-09-17
    • Related Report
      2014 Research-status Report
  • [Presentation] 光アフィニティー蛍光ラベル法による構造情報に基づいた結合解析2014

    • Author(s)
      友廣 岳則, 増田 宗太, 森本 正大, 山口 昇太, 千葉 順哉, 畑中 保丸
    • Organizer
      第36回日本光医学・光生物学会
    • Place of Presentation
      吹田市
    • Year and Date
      2014-07-25 – 2014-07-26
    • Related Report
      2014 Research-status Report
  • [Presentation] C1位カルボキシ基の誘導化によるシアル酸アナローグの開発2014

    • Author(s)
      中山純、橋田まみ、志村みさき、千葉順哉、友廣岳則、畑中保丸
    • Organizer
      日本薬学会第134回年会
    • Place of Presentation
      熊本
    • Related Report
      2013 Research-status Report
  • [Presentation] A Mild Coupling of Thioamide and Sulfonylazide as a Novel Click Reaction without Activation Additives2013

    • Author(s)
      Muhammad Aswad、加藤日奈、中山純、千葉順哉、友廣岳則、畑中保丸
    • Organizer
      日本ケミカルバイオロジー学会第8回年会
    • Place of Presentation
      東京
    • Related Report
      2013 Research-status Report
  • [Presentation] チオアミドとスルホニルアジドによる新規クリック型反応2013

    • Author(s)
      Muhammad Aswad、千葉順哉、友廣岳則、畑中保丸
    • Organizer
      日本薬学会北陸支部だい125回例会
    • Place of Presentation
      金沢
    • Related Report
      2013 Research-status Report
  • [Presentation] チオアミドを利用した水中での無触媒クリック型反応2013

    • Author(s)
      千葉順哉、畑中保丸
    • Organizer
      平成25年度中部地区医療・バイオ系シーズ発表会
    • Place of Presentation
      名古屋
    • Related Report
      2013 Research-status Report
  • [Book] e-EROS Encyclopedia of Reagents for Organic Synthesis2015

    • Author(s)
      Junya Chiba, Takenori Tomohiro, Yasumaru Hatanaka
    • Total Pages
      4
    • Publisher
      Wiley
    • Related Report
      2015 Research-status Report
  • [Remarks] 富山大学薬学部 生体認識化学研究室 ホームページ

    • URL

      http://www.pha.u-toyama.ac.jp/anachem/anachem/homu.html

    • Related Report
      2016 Annual Research Report 2015 Research-status Report 2014 Research-status Report
  • [Remarks] 富山大学薬学部 生体認識化学研究室 ホームページ

    • URL

      http://www.pha.u-toyama.ac.jp/anachem/anachem/homu.html

    • Related Report
      2013 Research-status Report
  • [Patent(Industrial Property Rights)] 2-デオキシ-2,3-ジデヒドロシアル酸誘導体およびその製造法2014

    • Inventor(s)
      畑中 保丸, 千葉 順哉, 友廣 岳則, 中山 純
    • Industrial Property Rights Holder
      富山大学
    • Industrial Property Rights Type
      特許
    • Industrial Property Number
      2014-227212
    • Filing Date
      2014-11-07
    • Related Report
      2014 Research-status Report
  • [Patent(Industrial Property Rights)] チオアミド誘導体2014

    • Inventor(s)
      千葉 順哉, 友廣 岳則, 畑中 保丸
    • Industrial Property Rights Holder
      富山大学
    • Industrial Property Rights Type
      特許
    • Industrial Property Number
      2014-207775
    • Filing Date
      2014-10-09
    • Related Report
      2014 Research-status Report
  • [Patent(Industrial Property Rights)] スルホニルアジド誘導体およびアシルスルホンアミド誘導体の製造方法並びにそれらの利用2013

    • Inventor(s)
      畑中保丸、千葉順哉、友廣岳則
    • Industrial Property Rights Holder
      国立大学法人富山大学
    • Industrial Property Rights Type
      特許
    • Filing Date
      2013-04-22
    • Acquisition Date
      2017-03-24
    • Related Report
      2016 Annual Research Report
  • [Patent(Industrial Property Rights)] スルホニルアジド誘導体およびアシルスルホンアミド誘導体の製造方法並びにそれらの利用2013

    • Inventor(s)
      畑中保丸、千葉順哉、友廣岳則
    • Industrial Property Rights Holder
      富山大学
    • Industrial Property Rights Type
      特許
    • Industrial Property Number
      2013-089114
    • Filing Date
      2013-04-22
    • Related Report
      2013 Research-status Report
  • [Patent(Industrial Property Rights)] 2-デオキシ-2,3-ジデヒドロシアル酸誘導体およびその製造法2013

    • Inventor(s)
      畑中保丸、千葉順哉、友廣岳則、中山純
    • Industrial Property Rights Holder
      富山大学
    • Industrial Property Rights Type
      特許
    • Industrial Property Number
      2013-236357
    • Filing Date
      2013-11-15
    • Related Report
      2013 Research-status Report

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Published: 2014-07-25   Modified: 2019-07-29  

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