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Rational Development of Novel Hemagglutinin-based Influenza Virus Inhibitors

Research Project

Project/Area Number 26460158
Research Category

Grant-in-Aid for Scientific Research (C)

Allocation TypeMulti-year Fund
Section一般
Research Field Drug development chemistry
Research InstitutionHoshi University

Principal Investigator

TSUBUKI Masayoshi  星薬科大学, 薬学部, 教授 (90163865)

Project Period (FY) 2014-04-01 – 2017-03-31
Project Status Completed (Fiscal Year 2016)
Budget Amount *help
¥4,550,000 (Direct Cost: ¥3,500,000、Indirect Cost: ¥1,050,000)
Fiscal Year 2016: ¥780,000 (Direct Cost: ¥600,000、Indirect Cost: ¥180,000)
Fiscal Year 2015: ¥1,430,000 (Direct Cost: ¥1,100,000、Indirect Cost: ¥330,000)
Fiscal Year 2014: ¥2,340,000 (Direct Cost: ¥1,800,000、Indirect Cost: ¥540,000)
Keywordsインフルエンザ / ヘマグルチニン / ムメフラール / 不斉合成 / キラル分割 / 共結晶 / 構造活性相関 / 全合成
Outline of Final Research Achievements

Influenza A virus infects cells by the action of hemagglutinin (HA) and neuraminidase (NA). Mumefural (MF), isolated from Japanese apricot extract, is the first compound which shows inhibitory effect against both HA and NA activities of H1N1 influenza virus (A/Narita/1/2009). For the development of new anti-influenza drugs, total synthesis of (±)-MFwas achieved in 6 steps and 80 derivatives of MF were prepared. Their structure-activity relationship studies have revealed hydroxy dicarboxylic acid moiety was important for expression of the inhibition activity. The derivatives with bulky ester moiety improved the activity. A new compound 10 having adamantane framework on the ester part was synthesized, and its activity was 10 times more potent than that of MF. In addition, a 7-step asymmetric synthesis was developed, and both enantiomers were synthesized starting from (S) and (R)-malic acids. We have confirmed (S)-MF has an inhibitory activity 2 times stronger than that of (R)-MF.

Report

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

    (7 results)

All 2017 2016 2015 2014

All Presentation (7 results)

  • [Presentation] 抗インフルエンザウイルス活性を有する mumefural 誘導体の構造活性相関研究2017

    • Author(s)
      加藤裕也, 横田智洋, Nongluk SRIWILAIJAROEN, 横江弘雅, 鈴木康夫, 常盤広明, 津吹政可
    • Organizer
      第137回日本薬学会年会
    • Place of Presentation
      仙台
    • Year and Date
      2017-03-24
    • Related Report
      2016 Annual Research Report
  • [Presentation] 梅エキス抽出物を先導化合物とした新規作用機序を示す抗インフルエンザ薬の開発2016

    • Author(s)
      加藤裕也, 横田智洋, Nongluk SRIWILAIJAROEN, 横江弘雅, 鈴木康夫, 常盤広明, 津吹政可
    • Organizer
      第136年会日本薬学会年会
    • Place of Presentation
      横浜
    • Year and Date
      2016-03-26
    • Related Report
      2015 Research-status Report
  • [Presentation] 梅エキスを先導化合物とした抗インフルエンザ阻害薬の構造活性相関研究2015

    • Author(s)
      加藤裕也, 横田智洋, Nongluk Sriwilaijaroen, 横江弘雅, 鈴木康夫, 常盤広明, 津吹政可
    • Organizer
      第59回日本薬学会関東支部大会
    • Place of Presentation
      日本大学薬学部
    • Year and Date
      2015-09-12
    • Related Report
      2015 Research-status Report
  • [Presentation] 新規マルチターゲット抗インフルエンザ阻害薬の構造活性相関研究2015

    • Author(s)
      横田智洋, 細沢拓未, 石坪江梨花, 加藤 裕也, 五十嵐学, Karl N. Kirshner, Nongluk Sriwilaijaroen, 横江弘雅, 鈴木康夫, 常盤広明2、津吹政可
    • Organizer
      日本薬学会第135年会
    • Place of Presentation
      神戸学院大学
    • Year and Date
      2015-03-26 – 2015-03-28
    • Related Report
      2014 Research-status Report
  • [Presentation] 食品由来の天然物を先導化合物とした新規マルチターゲット抗インフルエンザ薬の合理的設計開発2014

    • Author(s)
      石坪江梨花,細沢拓未,Karl N. Kirshner,Nongluk Sriwilaijaroen,横江弘雅, 津吹政可, 鈴木康夫,常盤広明
    • Organizer
      第32回メディシナルケミストリーシンポジウム
    • Place of Presentation
      神戸国際会議場
    • Year and Date
      2014-11-26 – 2014-11-28
    • Related Report
      2014 Research-status Report
  • [Presentation] 新規マルチターゲット抗インフルエンザ阻害剤の開発2014

    • Author(s)
      細沢拓未 、石坪江梨花、五十嵐学、Karl N. Kirshner、Nongluk Sriwilaijaroen、横江弘雅、津吹政可、鈴木康夫、常盤広明
    • Organizer
      創薬懇話会2014 in 岐阜
    • Place of Presentation
      長良川温泉ホテルパーク
    • Year and Date
      2014-07-10 – 2014-07-11
    • Related Report
      2014 Research-status Report
  • [Presentation] Development of Novel Multitarget Inhibitor for Glycoproteins of Influenza Virus2014

    • Author(s)
      Erika Ishitsubo, Takumi Hosozawa, Karl N. Kirshner, Nongluk Sriwilaijaroen, Hiromasa Yokoe, Masayoshi Tubuki, Yasuo Suzuki, Hiroaki Tokiwa
    • Organizer
      第9回糖転移酵素に関する国際シンポジウム
    • Place of Presentation
      ポルト
    • Year and Date
      2014-06-18 – 2014-06-21
    • Related Report
      2014 Research-status Report

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Published: 2014-04-04   Modified: 2018-03-22  

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