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Electrochemical oxidation of aromatic compounds towards effective biologically active substances

Research Project

Project/Area Number 17510182
Research Category

Grant-in-Aid for Scientific Research (C)

Allocation TypeSingle-year Grants
Section一般
Research Field Living organism molecular science
Research InstitutionKeio University

Principal Investigator

HISHIYAMA Shigcru  Keio University, Faculty of Science and Technology, Professor, 理工学部, 教授 (20137988)

Co-Investigator(Kenkyū-buntansha) MAKI Shojiro  The University of Electro-communications, Faculty of Electro-communications, Research Associate, 電気通信学部, 助手 (20266349)
Project Period (FY) 2005 – 2006
Project Status Completed (Fiscal Year 2006)
Budget Amount *help
¥3,500,000 (Direct Cost: ¥3,500,000)
Fiscal Year 2006: ¥1,100,000 (Direct Cost: ¥1,100,000)
Fiscal Year 2005: ¥2,400,000 (Direct Cost: ¥2,400,000)
Keywordsphenolic oxidation / natural products / anodic oxidation / diaryl ether / spiroisoxazole / thallium salt / hypervalent iodine / mangostin / ユーリパミド / 抗MRSA / ニトレニウムイオン / 環境対応 / 生理活性 / 有機化学 / 有機電気化学 / 全合成
Research Abstract

In the research project, anodic oxidation of phenol and related derivatives provided the following results.
1.In construction of the diaryl ether linkage shared by the isodityrosine-class natural products such as vancomycin, optimization of cyclization reactions employing thallium(III) salt was performed to provide the eurypamide derivative in quantitative yield. It was revealed that the cyclic derivative effectively increased the anti-MRSA activity of imipenem. Electrochemical generation of Tl(III) from Tl(I) was succeeded, and further efforts to make its catalytic system is in progress. In addition, galeon, a cytotoxic diaryl ether derivative of plant origin, was synthesized by controlling halogen-substituent to provide expected cyclization direction, and to introduce a required functional group.
2.Upon comparing with natural verbenachalcone carrying the diaryl ether linkage, synthetic derivatives exhibited effective enhancement or inhibitory activity of NFG-mediated neurite outgrowth from PC12D cell.
3.The absolutely optically active aerothionin, aeroplysinin-1, and their enantiomers were synthesized by diastereomeric-separation techniques.
4.Phenolic oxidation of mangostins provided a series of dienone-type products. Reactivities of phenol functions are evaluated.
5.Anodic oxidation of iodobenzene provided a hyper-valent iodine species, which was used as an effective oxidant.

Report

(3 results)
  • 2006 Annual Research Report   Final Research Report Summary
  • 2005 Annual Research Report
  • Research Products

    (32 results)

All 2007 2006 2005

All Journal Article (29 results) Book (1 results) Patent(Industrial Property Rights) (2 results)

  • [Journal Article] 新規生物活性物質を目指す有機電解合成2007

    • Author(s)
      西山 繁
    • Journal Title

      化学と生物 45・3

      Pages: 191-196

    • NAID

      10018572894

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2006 Final Research Report Summary
  • [Journal Article] Lignan and neoligna, in Natural Products-Plants-(S. Yamamura and K. Hasegawa Ed.) in Japanese2007

    • Author(s)
      S.Nishiyama
    • Journal Title

      I. P. C. Publisher

      Pages: 341-349

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2006 Final Research Report Summary
  • [Journal Article] Electrochemical synthesis towards new bioactive substances. in Japanese2007

    • Author(s)
      S.Nishiyama
    • Journal Title

      Kagaku to Seibutsu 45/3

      Pages: 191-196

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2006 Final Research Report Summary
  • [Journal Article] Total synthesis, structural revision and biological evaluation of calafianin, a marine spiroisoxazoline from the sponge, Aplysina gerardocgreeni.2006

    • Author(s)
      T.Ogamino
    • Journal Title

      Bull Chem. Soc. Jpn. 79・1

      Pages: 134-139

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2006 Final Research Report Summary
  • [Journal Article] Asymmetric synthesis of aerothionin, a marine dimeric spiroisoxazoline natural product, employing optically active spiroisoxazoline derivative2006

    • Author(s)
      T.Ogamino
    • Journal Title

      Tetrahedron Lett. 47・5

      Pages: 727-731

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2006 Final Research Report Summary 2005 Annual Research Report
  • [Journal Article] Synthesis of verbenachalcone congeners and their biological assessment against activation of the NGF-mediated neurite outgrowth of PC12D cells activity2006

    • Author(s)
      T.Tanabe
    • Journal Title

      Bioorg. Med, Chem. 14・8

      Pages: 2753-2762

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2006 Final Research Report Summary
  • [Journal Article] Synthesis and biological assessment of hemiacetal spiro derivatives towards development of efficient chemotherapeutic agent2006

    • Author(s)
      T.Ogamino
    • Journal Title

      Sci. Tech. Adv. Materials 7・2

      Pages: 175-183

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2006 Final Research Report Summary
  • [Journal Article] Oxidation of mangostins, the naturally occurring xanthone derivatives carrying diverse biological activities2006

    • Author(s)
      Y.Nishihama
    • Journal Title

      Electrochemistry 74・8

      Pages: 6505-6507

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2006 Final Research Report Summary
  • [Journal Article] Solid-phase synthesis and biological activities of biphenyl ether-containing cyclic oligopeptides2006

    • Author(s)
      K.Nakamura
    • Journal Title

      Peptide Science 2005, The Japanese peptide Society

      Pages: 127-130

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2006 Final Research Report Summary
  • [Journal Article] Oxidative synthesis of azacyclic derivatives through the nitrenium ion : application of a hypervalent iodine species electrochemically generated from iodobenzene2006

    • Author(s)
      Y.Amano
    • Journal Title

      Tetrahedron Lett. 47・37

      Pages: 6505-6507

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2006 Final Research Report Summary
  • [Journal Article] Oxidative cyclization of isodityrosine tripeptides with electrochemically generated thallium (III) ion2006

    • Author(s)
      T.Tanabe
    • Journal Title

      HETEROCYCLES 69・1

      Pages: 113-118

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2006 Final Research Report Summary
  • [Journal Article] Total synthesis, structural revision and biological evaluation of calafianin, a marine spiroisoxazoline from the sponge, Aplysina gerardogreeni2006

    • Author(s)
      T.Ogamino
    • Journal Title

      Bull Chem. Soc. Jpn. 79/1

      Pages: 134-139

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2006 Final Research Report Summary
  • [Journal Article] Asymmetric synthesis of aerothionin, a marine dimeric spiroisoxazoline natural product, employing optically active spiroisoxazoline derivative.2006

    • Author(s)
      T.Ogamino
    • Journal Title

      Tetrahedron Lett. 47/5

      Pages: 727-731

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2006 Final Research Report Summary
  • [Journal Article] Synthesis of verbenachalcone congeners and their biological assessment against activation of the NGF-mediated neurite outgrowth of PC 12D cells activity.2006

    • Author(s)
      T.Tanabe
    • Journal Title

      Bioorg. Med, Chem. 14/8

      Pages: 2753-2762

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2006 Final Research Report Summary
  • [Journal Article] Synthesis and biological assessment of hemiacetal spiro derivatives towards development of efficient chemotherapeutic agent.2006

    • Author(s)
      T.Ogamino
    • Journal Title

      Sci. Tech. Adv. Materials. 7/2

      Pages: 175-183

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2006 Final Research Report Summary
  • [Journal Article] Oxidation of mangostins, the naturally occurring xanthone derivatives carrying diverse biological activities.2006

    • Author(s)
      Y.Nishihama
    • Journal Title

      Electrochemistry 74/8

      Pages: 609-611

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2006 Final Research Report Summary
  • [Journal Article] Solid-phase synthesis and biological activities of biphenyl ether-containing cyclic oligopeptides.2006

    • Author(s)
      K.Nakamura
    • Journal Title

      Peptide Science 2005 (The Japanese peptide Society)

      Pages: 127-130

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2006 Final Research Report Summary
  • [Journal Article] Oxidative synthesis of azacyclic derivatiyes through the nitrenium ion : application of a hypervalent iodine species electrochemically generated from iodobenzene.2006

    • Author(s)
      Y.Amano
    • Journal Title

      Tetrahedron Lett. 47/37

      Pages: 6505-6507

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2006 Final Research Report Summary
  • [Journal Article] Oxidative cyclization of isodityrosine tripeptides with electrochemically generated thallium (III) ion.2006

    • Author(s)
      T.Tanabe
    • Journal Title

      HETEROCYCLES 69

      Pages: 113-118

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2006 Final Research Report Summary
  • [Journal Article] Oxidation of mangostins, the naturally occurring xanthone derivatives carrying diverse biological activities.2006

    • Author(s)
      Y.Nishiyama
    • Journal Title

      Electrochemistry 74/8

      Pages: 609-611

    • NAID

      10017389959

    • Related Report
      2006 Annual Research Report
  • [Journal Article] Solid-phase synthesis and biological activities of biphenyl ether-containing cyclic oligopeptides.2006

    • Author(s)
      K.Nakamura
    • Journal Title

      Peptide Science 2005, The Japanese peptide Society

      Pages: 127-130

    • Related Report
      2006 Annual Research Report
  • [Journal Article] Oxidative synthesis of azacyclic derivatives through the nitrenium ion : application of a hypervalent iodine species electrochemically generated from iodobenzene.2006

    • Author(s)
      Y.Amano
    • Journal Title

      Tetrahedron Lett. 47/37

      Pages: 6505-6507

    • Related Report
      2006 Annual Research Report
  • [Journal Article] Oxidative cyclization of isodityrosine tripeptides with electrochemically generated thallium(III) ion.2006

    • Author(s)
      T.Tanabe
    • Journal Title

      HETEROCYCLES 69/1

      Pages: 113-118

    • Related Report
      2006 Annual Research Report
  • [Journal Article] Total synthesis, structural revision and biological evaluation of calafianin, a marine spiroisoxazoline from the sponge, Aplysina gerardogreeni.2006

    • Author(s)
      T.Ogamino
    • Journal Title

      Bull Chem.Soc.Jpn. 79・1

      Pages: 134-139

    • Related Report
      2005 Annual Research Report
  • [Journal Article] Synthesis of verbenachalcone congeners and their biological assessment against activation of the NGF-mediated neurite outgrowth of PC12D cells activity2006

    • Author(s)
      T.Tanabe
    • Journal Title

      Bioorg.Med, Chem. 14・8

      Pages: 2753-2762

    • Related Report
      2005 Annual Research Report
  • [Journal Article] Synthesis and biological assessment of hemiacetal spiro derivatives towards development of efficient chemotherapeutic agent2006

    • Author(s)
      T.Ogamino
    • Journal Title

      Sci.Tech.Adv.Materials (印刷中)

    • Related Report
      2005 Annual Research Report
  • [Journal Article] Discovery of halogenated eurypamide B analogues as inhibitors of lipid droplet accumulation in macrophages.2005

    • Author(s)
      R.Obata
    • Journal Title

      Bioorg. Med. Chem. Lett. 15・19

      Pages: 4189-4191

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2006 Final Research Report Summary
  • [Journal Article] Discovery of halogenated eurypamide B analogues as mhibitors of lipid droplet accumulation in macrophaees.2005

    • Author(s)
      R.Obata
    • Journal Title

      Bioorg. Med. Chem. Lett. 15/19

      Pages: 4189-4191

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2006 Final Research Report Summary
  • [Journal Article] Discovery of halogenated eurypamide B analogues as inhibitors of lipid droplet accumulation in macrophages.2005

    • Author(s)
      R.Obata
    • Journal Title

      Bioorg.Med.Chem.Lett. 15・19

      Pages: 4189-4191

    • Related Report
      2005 Annual Research Report
  • [Book] 天然物化学-植物編-(山村庄亮、長谷川宏司編)2007

    • Author(s)
      西山 繁
    • Total Pages
      428
    • Publisher
      アイピーシー出版部
    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2006 Final Research Report Summary
  • [Patent(Industrial Property Rights)] 環状イソジチロシン誘導体化合物2005

    • Inventor(s)
      西山繁
    • Industrial Property Rights Holder
      西山繁
    • Filing Date
      2005-09-30
    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2006 Final Research Report Summary
  • [Patent(Industrial Property Rights)] 環状イソジチロシン誘導体化合物2005

    • Inventor(s)
      西山 繁
    • Industrial Property Rights Holder
      西山 繁
    • Filing Date
      2005-09-30
    • Related Report
      2005 Annual Research Report

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Published: 2005-04-01   Modified: 2016-04-21  

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