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Synthesis of Nucleoside Derivatives Applicable to Nucleic Acid Medicine

Research Project

Project/Area Number 24590143
Research Category

Grant-in-Aid for Scientific Research (C)

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

Principal Investigator

YOSHIMURA Yuichi  東北薬科大学, 薬学部, 教授 (00230813)

Project Period (FY) 2012-04-01 – 2015-03-31
Project Status Completed (Fiscal Year 2014)
Budget Amount *help
¥5,330,000 (Direct Cost: ¥4,100,000、Indirect Cost: ¥1,230,000)
Fiscal Year 2014: ¥1,560,000 (Direct Cost: ¥1,200,000、Indirect Cost: ¥360,000)
Fiscal Year 2013: ¥1,560,000 (Direct Cost: ¥1,200,000、Indirect Cost: ¥360,000)
Fiscal Year 2012: ¥2,210,000 (Direct Cost: ¥1,700,000、Indirect Cost: ¥510,000)
KeywordsNucleoside / aniti-HIV / antiherpes / Nucleic acid medicine / ヌクレオシド / 4'-チオヌクレオシド / グリコシル化反応 / 4-チオ糖 / 抗HIV活性 / スタブジン / nucleoside / nucleotide / antiviral
Outline of Final Research Achievements

To develop nucleoside derivatives applicable to introduce an oligonucleotide which can be used as nucleic acid medicine, design and synthesis of new nucleosides were investigated. We designed the following three nucleoside derivatives: 1) dihydropyranonucleoside, 2) L-threopentofuranosyl nucleoside, 3) 3’-deoxy-4’-thionucleoside. L-Threopentofuranosyl nucleoside was further converted to the corresponding nucleoside phosphonate derivative. All the nucleoside derivatives obtained were evaluated their antiviral activity including HIV.

Report

(4 results)
  • 2014 Annual Research Report   Final Research Report ( PDF )
  • 2013 Research-status Report
  • 2012 Research-status Report
  • Research Products

    (22 results)

All 2015 2014 2013 2012

All Journal Article (5 results) (of which Peer Reviewed: 5 results,  Open Access: 1 results,  Acknowledgement Compliant: 1 results) Presentation (17 results) (of which Invited: 3 results)

  • [Journal Article] Construction of an isonucleoside on a 2,6-dioxobicyclo[3.2.0]-heptane skeleton2015

    • Author(s)
      Yuichi Yoshimura, Satoshi Kobayashi, Hitomi Kaneko, Takeshi Suzuki, Tomozumi Imamichi
    • Journal Title

      Molecules

      Volume: 20 Issue: 3 Pages: 4623-4634

    • DOI

      10.3390/molecules20034623

    • Related Report
      2014 Annual Research Report
    • Peer Reviewed / Open Access / Acknowledgement Compliant
  • [Journal Article] Pummerer型チオグリコシル化反応の開発とヌクレオシド合成への応用2014

    • Author(s)
      吉村 祐一
    • Journal Title

      東北薬科大学研究誌

      Volume: 61 Pages: 1-10

    • NAID

      110009896994

    • Related Report
      2014 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Synthesis of a Dihydropyranonucleoside Using an Oxidative GlycosylationReaction Mediated by Hypervalent Iodine2014

    • Author(s)
      Kan-no, H.; Saito, Y.; Omoto, S.; Minato, S.; Wakamatsu, H.; Natori, Y.; Imamichi, T.; Takahata, H.; Yoshimura, Y.
    • Journal Title

      Synthesis

      Volume: 46 Issue: 07 Pages: 879-886

    • DOI

      10.1055/s-0033-1340663

    • Related Report
      2013 Research-status Report
    • Peer Reviewed
  • [Journal Article] Design and Synthesis of A Nucleoside and A Phosphonate Analogue Constructed on A Branched-threo-tetrofuranose Skeleton2013

    • Author(s)
      Kiran, Y. B.; Wakamatsu, H.; Natori, Y.; Takahata, H.; Yoshimura, Y.
    • Journal Title

      Tetrahedron Letters

      Volume: 54 Issue: 30 Pages: 3949-3952

    • DOI

      10.1016/j.tetlet.2013.05.062

    • Related Report
      2013 Research-status Report
    • Peer Reviewed
  • [Journal Article] Recent Advances in Cyclonucleosides: C-Cyclonucleosides and Spore Photoproducts in Damaged DNA2012

    • Author(s)
      Yoshimura, Y.; Takahata, H.
    • Journal Title

      Molecules

      Volume: 17 Issue: 10 Pages: 11630-11654

    • DOI

      10.3390/molecules171011630

    • Related Report
      2012 Research-status Report
    • Peer Reviewed
  • [Presentation] Dvelopement of New Glycosylation Reactions and Its Application to the Synthesis of Nucleoside Derivatives2015

    • Author(s)
      Yuichi Yoshimura
    • Organizer
      3rd SNU Mini-Symposium on Medicinal Chemistry
    • Place of Presentation
      韓国,ソウル
    • Year and Date
      2015-02-06
    • Related Report
      2014 Annual Research Report
    • Invited
  • [Presentation] 3'-デオキシ-4'-チオヌクレオシド誘導体の合成研究2014

    • Author(s)
      伊藤 文,名取 良浩,若松 秀章,吉村 祐一
    • 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
    • Year and Date
      2014-11-26 – 2014-11-28
    • Related Report
      2014 Annual Research Report
  • [Presentation] Syntheses of Stavudine and Its 4’-Substituted Analogue Using Hypervalent Iodine Mediated Oxidative Glycosylation2014

    • Author(s)
      Yuichi Yoshimura, Hiroya Kan-no, Yoshihiro Natori, Yukako Saito, Hideaki Wakamatsu
    • Organizer
      第2回国際会議(兼)第7回 有機触媒シンポジウム
    • Place of Presentation
      東京
    • Year and Date
      2014-11-21 – 2014-11-22
    • Related Report
      2014 Annual Research Report
  • [Presentation] 新規酸化的グリコシル化反応を利用したヌクレオシド誘導体の合成2014

    • Author(s)
      菅野 裕也,植松 拓也,若松 秀章,名取 良浩,斎藤 有香子,吉村 祐一,高畑 廣紀
    • Organizer
      日本薬学会第134年会
    • Place of Presentation
      熊本
    • Related Report
      2013 Research-status Report
  • [Presentation] 3'-デオキシ-4'-チオヌクレオシドの合成研究2014

    • Author(s)
      伊藤 文,吉村 祐一,若松 秀章,名取 良浩,高畑 廣紀
    • Organizer
      日本薬学会第134年会
    • Place of Presentation
      熊本
    • Related Report
      2013 Research-status Report
  • [Presentation] Synthesis of Dihydropyranonucleoside Using Hypervalent Iodine Mediated Glycosylation as a Key Reaction2013

    • Author(s)
      Yuichi Yoshimura, Hiroya Kan-no, Hiroki Takahata
    • Organizer
      Advanced Molecular Transformations by Organocatalysts 1st International Conference & 6th Symposium on Organocatalysis
    • Place of Presentation
      大津
    • Related Report
      2013 Research-status Report
  • [Presentation] Design and Synthesis of Nucleoside Phosphonate Constructed on a Branched-tetrofuranose Skeleton2013

    • Author(s)
      Yuichi Yoshimura, Y. B. Kiran, Hideaki Wakamatsu, Yoshihiro Natori, Hiroki Takahata
    • Organizer
      The 40th International Symposium on Nucleic Acids Chemistry
    • Place of Presentation
      横浜
    • Related Report
      2013 Research-status Report
  • [Presentation] 3’-デオキシ-4’-チオヌクレオシド類の合成研究2013

    • Author(s)
      伊藤 文,吉村 祐一,高畑 廣紀
    • Organizer
      第30回有機合成化学セミナー
    • Place of Presentation
      岡山
    • Related Report
      2013 Research-status Report
  • [Presentation] 酸化的グリコシル化反応を利用したスタブジン及び4'-置換スタブジンの新規合成法2013

    • Author(s)
      菅野裕也,植松拓也,吉村祐一,高畑廣紀
    • Organizer
      第31回メディシナルケミストリーシンポジウム
    • Place of Presentation
      広島
    • Related Report
      2013 Research-status Report
  • [Presentation] 超原子価ヨウ素試薬を用いたグリコシル化反応の開発とヌクレオシド合成への応用2013

    • Author(s)
      菅野裕也,吉村祐一,Y. B. Kiran,名取良浩,斎藤有香子,高畑廣紀
    • Organizer
      日本薬学会第133年会
    • Place of Presentation
      横浜
    • Related Report
      2012 Research-status Report
  • [Presentation] 酸化的グリコシル化反応を利用したジヒドロピラノヌクレオシドの合成2012

    • Author(s)
      菅野裕也,吉村祐一,高畑廣紀
    • Organizer
      第29回有機合成化学セミナー
    • Place of Presentation
      静岡
    • Related Report
      2012 Research-status Report
  • [Presentation] 新規ヌクレオシド誘導体合成を指向したグリコシル化反応の開発2012

    • Author(s)
      吉村祐一
    • Organizer
      平成24年度化学系学協会東北支部大会
    • Place of Presentation
      秋田
    • Related Report
      2012 Research-status Report
    • Invited
  • [Presentation] 超原子価ヨウ素試薬を利用したグリコシル化反応の開発とヌクレオシド合成への応用2012

    • Author(s)
      菅野裕也,吉村祐一,高畑廣紀
    • Organizer
      第51回日本薬学会東北支部大会
    • Place of Presentation
      青森
    • Related Report
      2012 Research-status Report
  • [Presentation] 超原子価ヨウ素試薬を利用したグリコシル化反応の開発2012

    • Author(s)
      吉村祐一,菅野裕也,Y. B. Kiran,名取良浩,斎藤有香子,高畑廣紀
    • Organizer
      第5回有機触媒シンポジウム
    • Place of Presentation
      東京
    • Related Report
      2012 Research-status Report
  • [Presentation] Synthetic Study of Novel Nucleoside Phosphonate Analog as a Potential Anti-HIV Agent2012

    • Author(s)
      Y. B. Kiran, Yuichi Yoshimura, Yoshihiro Natori, Hiroki Takahata
    • Organizer
      IKCOC-12
    • Place of Presentation
      京都
    • Related Report
      2012 Research-status Report
  • [Presentation] 新規ヌクレオシドホスホネート誘導体の合成研究2012

    • Author(s)
      吉村祐一,Y. B. Kiran,高畑廣紀
    • Organizer
      第30回メディシナルケミストリーシンポジウム
    • Place of Presentation
      東京
    • Related Report
      2012 Research-status Report
  • [Presentation] Development of Oxidative Glycosylation Reaction for Nucleoside Synthesis Based on Hypervalent Iodine Chemistry2012

    • Author(s)
      Yuichi Yoshimura
    • Organizer
      First Japan-USA Organocatalytic Symposium
    • Place of Presentation
      ホノルル,ハワイ
    • Related Report
      2012 Research-status Report
    • Invited

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Published: 2013-05-31   Modified: 2019-07-29  

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