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A new synthetic development of the bioactive benzo[c]phenanthridines based on a microwave-assisted electrocyclic reaction of aza 6π-electron system

Research Project

Project/Area Number 20590026
Research Category

Grant-in-Aid for Scientific Research (C)

Allocation TypeSingle-year Grants
Section一般
Research Field Chemical pharmacy
Research InstitutionFukuyama University

Principal Investigator

SATOSHI Hibino  Fukuyama University, 薬学部, 教授 (60112885)

Co-Investigator(Kenkyū-buntansha) CHOSHI Tominari  福山大学, 大学院・薬学研究科・薬学部, 准教授 (10248297)
SHUHEI Azuma  福山大学, 薬学部, 助手 (30509287)
Project Period (FY) 2008 – 2010
Project Status Completed (Fiscal Year 2010)
Budget Amount *help
¥4,680,000 (Direct Cost: ¥3,600,000、Indirect Cost: ¥1,080,000)
Fiscal Year 2010: ¥1,690,000 (Direct Cost: ¥1,300,000、Indirect Cost: ¥390,000)
Fiscal Year 2009: ¥1,430,000 (Direct Cost: ¥1,100,000、Indirect Cost: ¥330,000)
Fiscal Year 2008: ¥1,560,000 (Direct Cost: ¥1,200,000、Indirect Cost: ¥360,000)
Keywordsbenzo[c]phenanthridine alkaloid / 電子環状反応 / アザ6π電子系 / マイクロ波照射 / β-テトラロン / nornitidine / noravicine / isodecarine / norsanguinarine / norchelerythrine / zanthoxyline / broussonpapyrine / chelerythrine / X-線結晶構造解析 / マイクロ波照射下反応 / 全合成 / 構造解析 / benzo[c]phenanthridine / Suzuki-Miyaura reaction
Research Abstract

Total syntheses of the nor-type of benzo[c]phenanthridine alkaloids, nornitidine, noravicine, isodecarine, norchelerythrine, norsanguinarine, and zanthoxyline, and benzo[c]phenanthridine alkaloids, nitidine, avicine, sanguinarine, chelerythrine and broussonpapyrine were achieved. The key step was the construction of tetracyclic 11,12-dihydrobenzo[c]phenanthridine using a microwave-assisted electrocyclic reaction of the 2-cycloalkenylbenzaldoxime methyl ether as an aza 6π-electron system, which was derived in two steps from a Suzuk-Miyaura cross-coupling reaction of 2-brombenzaldehyde with (3,4-dihydro-6,7-methylenedioxynaphthyl)boronic acid pinacol ester. In addition, the exact structure of broussonpapyrine was determined to be chelerythrine by NMR spectral analysis.

Report

(4 results)
  • 2010 Annual Research Report   Final Research Report ( PDF )
  • 2009 Annual Research Report
  • 2008 Annual Research Report
  • Research Products

    (22 results)

All 2011 2010 2009 Other

All Journal Article (4 results) (of which Peer Reviewed: 4 results) Presentation (15 results) Book (1 results) Remarks (2 results)

  • [Journal Article] Total synthesis of benzo[c]phenanthridine alkaloids based on the microwave-assisted electrocyclic reaction of aza 6p-electron system, and structural revision of broussonpapyrine2011

    • Author(s)
      Yusuke Ishihara, Shuhei Azuma, Tominari, Choshi, Kakujirou Kohno, Kanako Ono, Hiroyuki Tsutsumi, Takashi Ishizu, Satoshi Hibino
    • Journal Title

      Tetrahedron 67

      Pages: 1320-1333

    • Related Report
      2010 Final Research Report
    • Peer Reviewed
  • [Journal Article] Total synthesis of benzo [c] phenanthridine alkaloids based on a microwave-assisted electrocyclic reaction of the aza 6π-electron system and structural revision of broussonpapyrine2011

    • Author(s)
      Y.Ishihara, S.Azuma, T.Choshi, K.Kohno, K.Ono, H.Tsutsumi, T.Ishizu, S.Hibino
    • Journal Title

      Tetrahedron

      Volume: 67巻 Pages: 1320-1333

    • NAID

      120006373263

    • Related Report
      2010 Annual Research Report
    • Peer Reviewed
  • [Journal Article] A new synthesis of the benzo[c]phenanthridines nornitidine, noravicine, and isodecarine, based on a microwave-asssted electrocyclic reaction of the aza 6p-electron system2009

    • Author(s)
      Kakujiro Kohno, Shuhei Azuma, Tominari Choshi, Junko Nobuhiro, Satoshi Hibino
    • Journal Title

      Tetrahedron Letters 50

      Pages: 590-592

    • Related Report
      2010 Final Research Report
    • Peer Reviewed
  • [Journal Article] A new synthesis of the benzo[c]phenanthridines nornitidine, noravicine, and isodecarine, based on a microwave-assisted electrocyclic reaction of the aza 6π-electron system2009

    • Author(s)
      Kakujiro Kohno, Shuhei Azuma, Tominari Choshi, Junko Nobuhiro, Satoshi Hibino
    • Journal Title

      Tetrahedron Letters 50

      Pages: 590-592

    • NAID

      120005952941

    • Related Report
      2008 Annual Research Report
    • Peer Reviewed
  • [Presentation] ベンゾフェナンスリジン型アルカロイドの合成研究2011

    • Author(s)
      石原裕介、倉田侑輝、町支臣成、波多江典之、岩村樹憲、日比野俐
    • Organizer
      日本薬学会第131年会
    • Place of Presentation
      静岡市
    • Related Report
      2010 Final Research Report
  • [Presentation] ベンゾフェナンスリジンアルカロイド型アルカロイドの合成研究2011

    • Author(s)
      石原裕介、倉田侑輝、町支臣成、波多江典之、岩村樹憲、目比野俐
    • Organizer
      日本薬学会第131年会
    • Place of Presentation
      静岡市(震災により参集は中止されたが要旨集発行により成立した。)
    • Related Report
      2010 Annual Research Report
  • [Presentation] ベンゾフェナンスリジンアルカロイド Broussonpapyrine の合成研究2010

    • Author(s)
      東修平, 他6名
    • Organizer
      日本薬学会第130年会
    • Place of Presentation
      桃太郎アリーナ(岡山市)
    • Year and Date
      2010-03-28
    • Related Report
      2009 Annual Research Report
  • [Presentation] ベンゾフェナンスリジンアルカロイドbroussonpapyrineの合成研究2010

    • Author(s)
      東修平、町支臣成、小野加奈子、河野覚次郎、日比野俐
    • Organizer
      日本薬学会第130年会
    • Place of Presentation
      岡山市
    • Related Report
      2010 Final Research Report
  • [Presentation] Synthesis of broussonpapyrine and zanthoxyline based on the microwave-asssited electrocyclic reaction of aza 6p-electron system, and their structures2010

    • Author(s)
      Satoshi Hibino, Shuhei Azuma, Yuhsuke Ishihara, Kanako Ono, Hiroyuki Tsutsumi, Takashi Ishizu, Kakujiro Kohno, Tominari Choshi
    • Organizer
      XIVth European Colloquium on Heterocyclic Chemistry
    • Place of Presentation
      Vienna, Austria.
    • Related Report
      2010 Final Research Report
  • [Presentation] 9,10-ジン置換ベンゾフェナンスリジン型アルカロイドの合成研究2010

    • Author(s)
      石原裕介、東修平、河野覚次郎、町支臣成、小野加奈子、日比野俐
    • Organizer
      第36回反応と合成の進歩シンポジウム
    • Place of Presentation
      名古屋市
    • Related Report
      2010 Final Research Report
  • [Presentation] 9,10-ジ置換ベンゾフェナンスリジン型アルカロイドの合成とその構造について2010

    • Author(s)
      石原裕介、東修平、河野覚次郎、町支臣成、小野加奈子、堤広之、石津隆、日比野俐
    • Organizer
      第49回日本薬学会・日本薬剤師会・日本病院薬剤師会中国四国支部学術大会
    • Place of Presentation
      米子市
    • Related Report
      2010 Annual Research Report 2010 Final Research Report
  • [Presentation] Synthesis of broussonpapyrine and zanthoxyline based on the microwave-assisted eletrocyclic reaction of aza 6π-electron system, and their structures2010

    • Author(s)
      S.Hibino, S.Azuma, Y.Ishihara, K.Ono, H.Tsutsumi, T.Ishizu, K.Kohno, T.Choshi
    • Organizer
      XXIVth European Colloquium on Heterocyclic Chemistry
    • Place of Presentation
      オーストリア、ウィーン
    • Related Report
      2010 Annual Research Report
  • [Presentation] 9,10-ジ置換ベンゾフェナンスリジン型アルカロイドの合成研究2010

    • Author(s)
      石原裕介、東修平、河野覚次郎、町支臣成、小野加奈子、堤広之、石津隆、日比野
    • Organizer
      第36回反応と合成の進歩シンポジウム
    • Place of Presentation
      名古屋市
    • Related Report
      2010 Annual Research Report
  • [Presentation] ベンゾフェナンスリジンアルカロイド Broussonpapyrine の合成研究2009

    • Author(s)
      東修平, 他4名
    • Organizer
      第48回日本薬学会・日本病院薬剤師会中国四国支部学術大会
    • Place of Presentation
      アスティとくしま(徳島市)
    • Year and Date
      2009-11-08
    • Related Report
      2009 Annual Research Report
  • [Presentation] A new synthesis of the benzo[c]phenanthridines, nornitidine, noravicine, and isodecarine, based on a microwave-assisted electrocyclic reaction of the aza 6π-electron system2009

    • Author(s)
      日比野俐, 他4名
    • Organizer
      22nd International Congress on Heterocyclic Chemistry
    • Place of Presentation
      The Delta Hotel and Convention Center(St.John's Canada)
    • Year and Date
      2009-08-04
    • Related Report
      2009 Annual Research Report
  • [Presentation] マイクロ波照射下aza-6π電子系電子環状反応を活用したbenzo[c]phenanthridine類の新規合成研究2009

    • Author(s)
      東修平, 町支臣成, 河野党次郎, 日比野俐
    • Organizer
      日本薬学会第129年会
    • Place of Presentation
      京都国際会館(京都市)
    • Year and Date
      2009-03-28
    • Related Report
      2008 Annual Research Report
  • [Presentation] マイクロ波照射下aza-6π電子系電子環状反応を活用したbenzo[c]phenanthridine類の新規合成研究2009

    • Author(s)
      東修平、町支臣成、河野覚次郎、日比野俐
    • Organizer
      日本薬学会第129年会
    • Place of Presentation
      京都市
    • Related Report
      2010 Final Research Report
  • [Presentation] A new synthesis of the benzo[c]phenanthridines nornitidine,noravicine, and isodecarine, based on a microwave-assisted electrocyclic reaction of the aza 6p-electron system2009

    • Author(s)
      Shuhei Azuma, Kakujiro Kohno, Tominari Choshi, Junko Nobuhiro, Satoshi Hibino
    • Organizer
      22nd International Congress on Heterocyclic Chemistry
    • Place of Presentation
      St. John's, Canada.
    • Related Report
      2010 Final Research Report
  • [Presentation] ベンゾフェナンスリジンアルカロイドBroussonpapyrineの合成研究2009

    • Author(s)
      東 修平、町支臣成、小野加奈子、河野覚次郎、日比野俐
    • Organizer
      第48回日本薬学会・日本薬剤師会・日本病院薬剤師会・中国四国支部学術大会
    • Place of Presentation
      徳島市
    • Related Report
      2010 Final Research Report
  • [Book] CBT対策と演習「医薬品化学」2009

    • Author(s)
      日比野俐
    • Total Pages
      27
    • Publisher
      廣川書店
    • Related Report
      2009 Annual Research Report
  • [Remarks] ホームページ等

    • URL

      http://www.fukuyama-u.ac.jp

    • Related Report
      2010 Final Research Report
  • [Remarks]

    • URL

      http://www.fukuyama-u.ac.jp/

    • Related Report
      2010 Annual Research Report

URL: 

Published: 2008-04-01   Modified: 2016-04-21  

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