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2011 Fiscal Year Final Research Report

Useful β-turn mimetics having three-dimensional diversity

Research Project

  • PDF
Project/Area Number 21390028
Research Category

Grant-in-Aid for Scientific Research (B)

Allocation TypeSingle-year Grants
Section一般
Research Field Drug development chemistry
Research InstitutionHokkaido University

Principal Investigator

SHUTO Satoshi  北海道大学, 大学院・薬学研究院, 教授 (70241346)

Co-Investigator(Kenkyū-buntansha) ARISAWA Mitsuhiro  北海道大学, 大学院・薬学研究院, 准教授 (40312962)
Project Period (FY) 2009 – 2011
Keywordsβターン / ペプチドミメティック / シクロプロパン / MC4 / Grb2
Research Abstract

The stereochemical diversity-oriented b-turn mimetics were designed and efficient and stereoselective synthetic method of them have been developed. Applying the mimetics to the development of melanocortin receptor ligands, we discovered a highly potent non-peptidic lead. Thus, the stereochemical diversity-oriented b-turn mimetics were shown to be useful in developing a non-peptidic lead, especially in cases where the binding conformation of the ligand and the structural data of the receptors are lacking or are poorly documented.

  • Research Products

    (17 results)

All 2012 2011 2010 2009

All Journal Article (6 results) (of which Peer Reviewed: 6 results) Presentation (10 results) Book (1 results)

  • [Journal Article] Cyclopropane-Based Stereochemical Diversity-Oriented Conformational Restriction Strategy : Histamine Analog swith the4-Amino-2, 3-methano-1-(1H-imidazol-4-yl) butane Structure as Highly PotentHistamine H_3 and/or H4 Receptor Ligands. Org2012

    • Author(s)
      M. Watanabe, T. Kobayashi, T. Hirokawa, A. Yoshida, Y. Ito, S. Yamada, N. Orimoto, Y. Yamasaki, M. Arisawa, S. Shuto
    • Journal Title

      Biomol. Chem

      Volume: 10 Pages: 736-745

    • DOI

      DOI:10.1039/C1OB06496G

    • Peer Reviewed
  • [Journal Article] Synthesis of a series of 3,4-methanoarginines as side-chainconformationally restricted analogues of arginine2011

    • Author(s)
      M. Watanabe, K. Yamaguchi, W. Tang, K. Yoshida, R. B. Silverman, M. Arisawa, S. Shuto
    • Journal Title

      Bioorg. Med. Chem

      Volume: 19 Pages: 5984-5988

    • URL

      http://www.ncbi.nlm.nih.gov/pubmed/21917467

    • Peer Reviewed
  • [Journal Article] Alkene isomerization/enamide-ene and diene metathesis for the construction ofindoles, quinolines, benzofurans and chromenes with a chiral cyclopropane substituent. Org2011

    • Author(s)
      T. Kobayashi, M. Arisawa, S. Shuto
    • Journal Title

      Biomol. Chem

      Volume: 9 Pages: 1219-1224

    • DOI

      DOI:10.1039/C0OB00597E

    • Peer Reviewed
  • [Journal Article] Investigation of the Bioactive Conformation of Histamine H_3 ReceptorAntagonists by the Cyclopropylic Strain-Based Conformational Restriction Strategy2010

    • Author(s)
      M. Watanabe, T. Hirokawa, T. Kobayashi, A. Yoshida, Y. Ito, S. Yamada, N. Orimoto, Y. Yamasaki, M. Arisawa, S. Shuto
    • Journal Title

      J. Med. Chem

      Volume: 53 Pages: 3585-3593

    • DOI

      DOI:10.1021/jm901848b

    • Peer Reviewed
  • [Journal Article] Synthesis and Structural and Pharmacological Properties of cyclopropane-based conformationally restricted analogs of 4-methylhistamine as histamine H_3/H_4 receptor ligands. Bioorg2010

    • Author(s)
      T. Kobayashi, M. Watanabe, A. Yoshida, S. Yamada, M. Ito, H. Abe, Y. Ito, M. Arisawa, S. Shuto
    • Journal Title

      Med. Chem

      Volume: 18 Pages: 1076-1082

    • URL

      http://www.ncbi.nlm.nih.gov/pubmed/20045649

    • Peer Reviewed
  • [Journal Article] Three-dimensional structure-activity relationship study of belactosin A and its stereo and regioisomers : development of potent proteasome inhibitors by the stereochemical diversity-oriented strategy. Org2009

    • Author(s)
      K. Yoshida, K. Yamaguchi, A. Mizuno, Y. Unno, A. Asai, T. Sone, H. Yokosawa, A. Matsuda, M. Arisawa, S. Shuto
    • Journal Title

      Biomol. Chem

      Volume: 7 Pages: 1868-1877

    • URL

      http://www.ncbi.nlm.nih.gov/pubmed/19590782

    • Peer Reviewed
  • [Presentation] Structure-Activity Relationship Study of Unnatural cis-Isomer of Belactosin A, a Potent Proteasome Inhibitor2011

    • Author(s)
      Shuhei, Kawamura, Yuka, Unno, Motohiro, Tanaka, Takuma, Sasaki, Akira, Asai, Mitsuhiro, Arisawa, and Satoshi, Shuto
    • Organizer
      AIMECS 11 8t AFMC International Medicinal Chemistry Symposium Frontier of Medicinal Science
    • Place of Presentation
      京王プラザホテル東京(東京都)
    • Year and Date
      20111129-1202
  • [Presentation] 三次元多様型配座制御法に基づくペプチドミメティックの設計.メラノコルチン受容体リガンドの創製-2011

    • Author(s)
      水野彰、三浦志帆、渡辺瑞貴、小田上剛直、小上裕二、有澤光弘、周東智
    • Organizer
      第37回反応と合成の進歩シンポジウム
    • Place of Presentation
      徳島大学(徳島市)
    • Year and Date
      20111100
  • [Presentation] Investigation of the bioactive conformation of Histamine H3/H4 receptor antagonists by the conformational restriction strategy2011

    • Author(s)
      Kobayashi, T. , Watanabe, M., Hirokawa, T., Yamada, S., Arisawa, M., Shuto, S.
    • Organizer
      8th AFMC International Medicinal Chemistry Symposium (AIMECS11)
    • Place of Presentation
      京王プラザホテル東京(東京都)
    • Year and Date
      20111100
  • [Presentation] Design of Stereochemical Diversity-Oriented Cyclopropane-Based Peptidomimetics : Development of Potent Melanocortin Receptor Ligands2011

    • Author(s)
      Mizuno, A.; Miura, S.; Watanabe, M.; Uchida, S.; Yamada, S.; Arisawa, M.; Shuto, S.
    • Organizer
      Otsu Conference 2011
    • Place of Presentation
      大津プリンスホテル(滋賀県)
    • Year and Date
      20111000
  • [Presentation] Stereochemical Diversity-Oriented Design of Cyclopropane-Based Peptidomimetics : Synthesis of Melanocortin Receptor Ligands2011

    • Author(s)
      Mizuno, A.; Miura, S.; Watanabe, M.; Uchida, S.; Yamada, S.; Arisawa, M.; Shuto, S.
    • Organizer
      28th Herbert C. Brown Lectures
    • Place of Presentation
      Purdue University (USA)
    • Year and Date
      20110400
  • [Presentation] 制がん性プロテアソーム阻害剤ベラクトシンAシス型立体異性体の構造活性相関研究2011

    • Author(s)
      川村周平、海野雄加、田中基裕、佐々木磨、浅井章良、有澤光弘、周東智
    • Organizer
      第131年会日本薬学会
    • Place of Presentation
      グランシップツインメッセ静岡(静岡県)
    • Year and Date
      20110328-31
  • [Presentation] Enamide-ene methasesis for constructing chiral 2-cyclopropylheterocycles : Indole, quinoline, benzofuran and chromene2010

    • Author(s)
      Kobayashi, T., Arisawa, M., Shuto, S.
    • Organizer
      240th American Chemical Society National Meeting
    • Place of Presentation
      Boston Convention & Exposition Center (USA)
    • Year and Date
      20100800
  • [Presentation] 光学活性シクロプロパンを有する複素環化合物合成法の開発2010

    • Author(s)
      小林嵩明、有澤光弘、周東智
    • Organizer
      日本薬学会第130年会
    • Place of Presentation
      岡山コンベンションセンター(岡山県)、岡山大学(岡山市)
    • Year and Date
      20100300
  • [Presentation] シクロプロパン歪みに基づくヒスタミンH3受容体リガンドの設計と活性配座解析2009

    • Author(s)
      小林嵩明、渡辺瑞貴、広川貴次、吉田徳、伊東由彦、山田静雄、有澤光弘、周東智
    • Organizer
      第28回メディシナルケミストリーシンポジウム
    • Place of Presentation
      東京大学(文京区)
    • Year and Date
      20091100
  • [Presentation] 立体多様性を鍵とするシクロプロパン型ペプチドミメティック-メラノコルチン受容体リガンドの創製研究-2009

    • Author(s)
      水野彰、梶原浩気、三浦志帆、渡辺瑞貴、吉田徳、内田信也、山田静雄、小田上剛直、小上裕二、有澤光弘、周東智
    • Organizer
      第7回次世代を担う有機化学シンポジウム
    • Place of Presentation
      大阪大学(吹田市)
    • Year and Date
      20090700
  • [Book] 有機医薬分子論2011

    • Author(s)
      周東智
    • Total Pages
      320
    • Publisher
      京都廣川書店出版

URL: 

Published: 2013-07-31  

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