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Synthetic studies of indolenine derivative with an asymmetric quaternary carbon

Research Project

Project/Area Number 20890129
Research Category

Grant-in-Aid for Young Scientists (Start-up)

Allocation TypeSingle-year Grants
Research Field Drug development chemistry
Research InstitutionNara Institute of Science and Technology

Principal Investigator

KAGAWA Natsuko  Nara Institute of Science and Technology, 大学院・薬学研究院, 助教 (60467686)

Project Period (FY) 2008 – 2009
Project Status Completed (Fiscal Year 2009)
Budget Amount *help
¥3,302,000 (Direct Cost: ¥2,540,000、Indirect Cost: ¥762,000)
Fiscal Year 2009: ¥1,560,000 (Direct Cost: ¥1,200,000、Indirect Cost: ¥360,000)
Fiscal Year 2008: ¥1,742,000 (Direct Cost: ¥1,340,000、Indirect Cost: ¥402,000)
Keywordsインドール / インドレニン / 互変異性体 / 立体選択性 / パラジウム / マグネシウム / ヨヒンビン / レゼルピン / 有機化学 / 複素環 / アリル化反応 / アルカロイド / 不斉炭素 / アリル化 / 国際情報交流 / アメリカ:スペイン
Research Abstract

Medicinal components in reserpine (hypotensive drugs & tranquilizers) and ajmaline (antiarrhythmic drugs) have a common chemical structure "indole", however possess different biological activities. An indole core in the reserpine was changed into an indolenine core by organic synthetic chemistry in order to clear a chemical role of indole. The molecular structure of indolenine was identified and characterized with scientific evidence.

Report

(4 results)
  • 2009 Annual Research Report   Final Research Report ( PDF )
  • 2008 Annual Research Report
  • Products Report
  • Research Products

    (18 results)

All 2013 2010 2009 2008

All Journal Article (6 results) (of which Peer Reviewed: 6 results) Presentation (12 results)

  • [Journal Article] Stereochemistry of C7-allyl yohimbine explored by X-ray crystallography2013

    • Author(s)
      加川 夏子
    • Journal Title

      Journal of Molecular Structure

      Volume: 1036 Pages: 133-143

    • DOI

      10.1016/j.molstruc.2012.09.074

    • Related Report
      Products Report
    • Peer Reviewed
  • [Journal Article] Rare earth triflates/chlorotrimethylsilane induced activation of triethylamine as a latent acetaldehyde anion : a new synthesis of α,β-unsaturated aldehydes2010

    • Author(s)
      Natsuko Kagawa, Yoshiko Sasaki, Hideo Kojima, Masahiro Toyota
    • Journal Title

      Tetrahedron Letters Vol.51, No.3

      Pages: 482-484

    • Related Report
      2009 Final Research Report
    • Peer Reviewed
  • [Journal Article] Rare earth triflates/chlorotrimethylsilane induced activation of triethylamine as a latent acetaldehyde anion : a new synthesis of α, β-unsaturated aldehydes2010

    • Author(s)
      加川夏子, 豊田真弘
    • Journal Title

      Tetrahedron Letters VOL.51

      Pages: 482-484

    • Related Report
      2009 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Rh(I)-Catalyzed CO Gas-Free Carbonylative Cyclization Reactions of Alkynes with 2-Bromophenylboronic Acids Using Formaldehyde2009

    • Author(s)
      Tsumoru Morimoto, Kae Yamasaki, Akihisa Hirano, Ken Tsutsumi, Natsuko Kagawa, Kiyomi Kakiuchi, Yasuyuki Harada, Yoshiya Fukumoto, Naoto Chatani, Takanori Nishioka
    • Journal Title

      Organic Letters Vol.11, No.8

      Pages: 1777-1780

    • Related Report
      2009 Final Research Report
    • Peer Reviewed
  • [Journal Article] Rh(I)-catalyzed CO gas-free carbonylative cyclization reactions of alkynes with 2-bromophenylboronic acids using formaldehyde2009

    • Author(s)
      森本積, 加川夏子
    • Journal Title

      Organic Letters VOL.11

      Pages: 1777-1780

    • Related Report
      2009 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Palladium-Catalyzed β-Allylation of 2, 3-Disubstituted Indoles2008

    • Author(s)
      加川 夏子
    • Journal Title

      Organic Letters 1 0

      Pages: 2381-2384

    • Related Report
      2008 Annual Research Report
    • Peer Reviewed
  • [Presentation] グアニジン触媒を用いた2,2-ジ置換キラルクロマン化合物の不斉合成研究2010

    • Author(s)
      徳能紗也香, 中西和嘉, 熊本卓哉, 加川夏子, 石川勉
    • Organizer
      日本薬学会第130年会
    • Place of Presentation
      岡山
    • Year and Date
      2010-03-28
    • Related Report
      2009 Final Research Report
  • [Presentation] 3-アリールアジリジン-2-カルボキシレートを利用したポドフィロトキシンの合成研究2010

    • Author(s)
      高橋正人, 加川夏子, 熊本卓哉, 石川勉
    • Organizer
      日本薬学会第130年会
    • Place of Presentation
      岡山
    • Year and Date
      2010-03-28
    • Related Report
      2009 Final Research Report
  • [Presentation] インドールのC3位選択的なアリル化反応におけるインドレニン成績体の安定性と立体選択性の発生メカニズムについて2010

    • Author(s)
      加川夏子
    • Organizer
      日本化学会第90春季年会
    • Place of Presentation
      東大阪 (大阪)
    • Year and Date
      2010-03-26
    • Related Report
      2009 Final Research Report
  • [Presentation] インドールのC3位選択的なアリル化反応におけるインドレニン成績体の安定性と立体選択性の発生メカニズムについて2010

    • Author(s)
      加川夏子
    • Organizer
      日本化学会第90春季年会
    • Place of Presentation
      近畿大学本部キャンパス(大阪府)
    • Year and Date
      2010-03-26
    • Related Report
      2009 Annual Research Report
  • [Presentation] グアニジン触媒を用いた2,2-ジ置換キラルクロマン化合物の不斉合成研究2009

    • Author(s)
      徳能紗也香, 中西和嘉, 熊本卓哉, 加川夏子, 石川勉
    • Organizer
      第35回反応と合成の進歩シンポジウム
    • Place of Presentation
      金沢
    • Year and Date
      2009-11-16
    • Related Report
      2009 Final Research Report
  • [Presentation] ミロエステロール合成に向けたドミノ環化を利用した鍵中間体の合成研究2009

    • Author(s)
      秋元麻友子, 熊本卓哉, 加川夏子, 石川勉
    • Organizer
      第53回香料・テルペンおよび精油化学に関する討論会
    • Place of Presentation
      生駒 (奈良)
    • Year and Date
      2009-11-08
    • Related Report
      2009 Final Research Report
  • [Presentation] ミロエステロール合成に向けたドミノ環化を利用した鍵中間体の合成研究2009

    • Author(s)
      秋元麻友子
    • Organizer
      香料・テルペンおよび精油化学に関する討論会
    • Place of Presentation
      奈良先端科学技術大学院大学(奈良県)
    • Year and Date
      2009-11-08
    • Related Report
      2009 Annual Research Report
  • [Presentation] The Synthetic Study of C3-Branched Indole : As an Approach to the Formation of Chiral Indolenine2008

    • Author(s)
      Ade Arsianti, Natsuko Kagawa, Tsumoru Morimoto, Kiyomi Kakiuchi
    • Organizer
      The 8^<th> GIST/NAIST Joint Symposium on Advanced Materials
    • Place of Presentation
      生駒 (奈良)
    • Year and Date
      2008-11-26
    • Related Report
      2009 Final Research Report
  • [Presentation] 立体障害性インドールに対するパラジウム触媒を用いたβ-アリル化によるインドレニン類の合成2008

    • Author(s)
      加川夏子, Jeremiah P. Malerich, Ye Zhu, Viresh H. Rawal
    • Organizer
      第38回複素環化学討論会
    • Place of Presentation
      福山 (広島)
    • Year and Date
      2008-11-21
    • Related Report
      2009 Final Research Report
  • [Presentation] 立体障害性インドールに対するパラジウム触媒を用いたβ-アリル化によるインドレニン類の合成2008

    • Author(s)
      加川 夏子
    • Organizer
      第3 8回複素環化学討論会
    • Place of Presentation
      福山-日本
    • Year and Date
      2008-11-21
    • Related Report
      2008 Annual Research Report
  • [Presentation] New Development and Requirement of Indole Chemistry-Syntheses of Indolenine Derivative2008

    • Author(s)
      Natsuko Kagawa, Jeremiah P. Malerich, Ye Zhu, Viresh H. Rawal
    • Organizer
      18^<th> International Symposium on Fine Chemistry and Functional Polymers (FCFP-XVIII) & IUPAC 4^<th> International Symposium on Novel Materials and Synthesis (NMS-IV)
    • Place of Presentation
      Zhenjiang (China)
    • Year and Date
      2008-10-16
    • Related Report
      2009 Final Research Report
  • [Presentation] New Development and Requirement of Indole Chemistry-Syntheses of Indolenine Derivatives2008

    • Author(s)
      加川 夏子
    • Organizer
      18^<th> International Symposium on Fine Chemistry and Functional Polymers 4^<th> IUPAC International Symposium on Novel Materials and their Synthesis
    • Place of Presentation
      鎮江-中国
    • Year and Date
      2008-10-16
    • Related Report
      2008 Annual Research Report

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Published: 2008-04-01   Modified: 2016-09-09  

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