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Study on Total Synthesis of Anti-tumorous Varacin and Application to Anti-tumor Drag

Research Project

Project/Area Number 05554015
Research Category

Grant-in-Aid for Developmental Scientific Research (B)

Allocation TypeSingle-year Grants
Research Field Organic chemistry
Research InstitutionIWATE UNIVERSITY

Principal Investigator

SATO Ryu  IWATE UNIVERSITY,FACULTY OF ENGINEERING,PROFFESOR, 工学部, 教授 (00003872)

Co-Investigator(Kenkyū-buntansha) SAINO Tetsushi  NIHON KAYAKU CO.RESEARCH CENTER OF DRAGS,GROUP LEADER, 医薬事業本部, 第二薬理グループ長
OGAWA Satoshi  IWATE UNIVERSITY,FACULTY OF ENGINEERING,ASSOCIATE PROFFESOR, 工学部, 助教授 (70224102)
Project Period (FY) 1993 – 1994
Project Status Completed (Fiscal Year 1994)
Budget Amount *help
¥10,000,000 (Direct Cost: ¥10,000,000)
Fiscal Year 1994: ¥3,000,000 (Direct Cost: ¥3,000,000)
Fiscal Year 1993: ¥7,000,000 (Direct Cost: ¥7,000,000)
KeywordsVaracin / Synthesis / Anti-tumor / Cyclic polysulfides / Benzopentathiepin / Biological activity / Lissoclinotoxin / Elemental Sulfur / 細胞毒性 / 子宮頸癌 / ベンゼンチオール / オルトリチオ化 / ベンゼンジチオール / 環状ポリスルフィド
Research Abstract

Recently, the characteristic chemical properties of cyclic polysulfides have attracted wide attention in the field of organosulfur chemistry. We have also reported new methods for the synthesis of benzopentathiepins and the related compounds. Furthermore, we have found many reactions for providing some heterocycles from such cyclic polysulfides. On the basis of these findings, our interests were directed to the synthesis of novel biologically active benzopentathiepin, for example, varacin and lissoclinotoxins, which were found in marine natural products and the total syntheses have been recently reported. Now, we wish to report an efficient synthesis and the biological properties of two novel benzopentathiepins, 6,7, -dimethoxybenzopentathiepin and 6-aminoethylbenzopentathiepin, which are partial structures of varacin, using our original method with elemental sulfur and gaseous ammonia.

Report

(3 results)
  • 1994 Annual Research Report   Final Research Report Summary
  • 1993 Annual Research Report
  • Research Products

    (22 results)

All Other

All Publications (22 results)

  • [Publications] Satoshi Ogawa, Naoki Yomoji,Shi-ichi Chida, and Ryu Sato: "An Effective and Selective Synthesis of Sterically Crowded Benzotrithioles from Benzodithiastannoles via Benzotrithiole-2-oxides" Chem. Lett.507-510 (1994)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1994 Final Research Report Summary
  • [Publications] Ryu Sato, Tetsuya Ohyama,and Satoshi Ogawa: "Efficient Synthesis and Biological Properties of New Benzopentathiepins" Heterocycles, in press.

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1994 Final Research Report Summary
  • [Publications] Naoki Yomoji, Shin-ichi Satoh, Satoshi Ogawa, and Ryu Sato: "First Example of Intramolecular Photochemical Oxygen Migration from Benzotrithiole 2-Oxides to Benzotrithiole 1-Oxides" Tetrahedron Lett.Vol.34. 673 (1993)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1994 Final Research Report Summary
  • [Publications] Ryu Sato, Akira Onodera, Shin-ichi Satoh, and Junko Kumagai: "Reaction of Cyclic Polysulfides with Alkene in the Presence of Lewis Acid" Phosphorus, Sulfur, and Silicon. Vol.74. 389 (1993)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1994 Final Research Report Summary
  • [Publications] Shin-ichi Chida, Takashi Yoshida, Takuya Shimizu, and Ryu Sato: "An Efficient and Convenient Method for the Synthesis of Cyclic Dithiosulfites" Sulfur Lett.Vol.16. 5 (1993)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1994 Final Research Report Summary
  • [Publications] Ryu Sato, Miyoshi Yamashita, Masato Hujiwara, Shin-ichi Chida and Satoshi Ogawa: "Oxidation of 2,2'-Spirobi (1,3-benzodithiole)" Sulfur Lett.Vol.16. 109 (1993)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1994 Final Research Report Summary
  • [Publications] Naoki Yomoji, Shouichi Takahashi, Shin-ichi Chida, Satoshi Ogawa, and Ryu Sato: "Oxidation of Benzotrithiole Analogues. Photochemical Rearrangement of Benzotrithiole 2-Oxides to Benzotrithiole 1-Oxides involving Intramolecular Oxygen Migration" J.Chem.Soc., Perkin Trans. 1. 1995 (1993)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1994 Final Research Report Summary
  • [Publications] Satoshi Ogawa, Sachiko Ohara, Yasushi Kawai, and Ryu Sato: "Synthesis and Molecular Structure of 3,4,13,14-Tetraselenatricyclo[14.4.0.0 ^<6,11>]-icosa-1 (16), 6,8,10,17,19-hexaene" Heterocycles. Vol.38. 491 (1994)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1994 Final Research Report Summary
  • [Publications] Satoshi Ogawa, Naoki Yomoji, Shin-ichi Chida, and Ryu Sato: "An Effective and Selective Synthesis of Sterically Crowded Benzotrithioles from Benzodithiastannoles via Benzotrithiole-2-oxides" Chem.Lett.507 (1994)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1994 Final Research Report Summary
  • [Publications] Ryu Sato, Masako Okanuma, Shin-ichi Chida, and Satoshi Ogawa: "Convenient Synthesis of Benzotrithiepins and Benzotrithiocins from Dithiols and Thiirans" Tetrahedron Lett.Vol.35. 891 (1994)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1994 Final Research Report Summary
  • [Publications] Satoshi Ogawa, Takamasa Kikuchi, Shigeya Niizuma, and Ryu Sato: "Preparation and Novel One-elctron Redox reactions of a New Stable 4,7-Diisopropylbenzo[1,2-d][1,2,3]triselenole and its Radical Cation Salt" J.Chem.Soc., Chem.Commun. 1593 (1994)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1994 Final Research Report Summary
  • [Publications] Satoshi Ogawa, Takamasa Kikuchi, Atsuko Sasaki, Shin-ich Chida, and Ryu Sato: "First Systematic Synthesis and Electrochemical Oxidation of 4,7-Diisopropyl-1,2,3-benzotrichalcogenoles Containing Both Sulfur and Selenium Atoms" Tetrahedron Lett.Vol.35. 5469 (1994)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1994 Final Research Report Summary
  • [Publications] Satoshi Ogawa, Masaki Sasaki, Takayuki Ogasawara, Ryu Sato, and Yasushi Kawai: "Synthesis, Structure, and Oxidation of 3,4-Dihydro-1,2,5-Benzotrithiepanes" J.Heteroatom Chem.in press.

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1994 Final Research Report Summary
  • [Publications] Satoshi Ogawa, Miyoshi Yamashita, and Ryu Sato: "New Tellurium Containing Five-Membered Trichalcogenaheterocycles Fused to Benzene Rings : A Convenient Method for Transformation of Dichalcogenatelluroles into Novel Tetrachalcogenocins" Tetrhedron Lett.in press.

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1994 Final Research Report Summary
  • [Publications] Satoshi Ogawa, Satoshi Saito, Takamasa Kikuchi, Yasushi Kawai, Shigeya Niizuma, and Ryu Sato: "Synthesis, Structure, and Oxidation of Novel 4,7-Disubstituted Benzotrithioles. Formation and Characterization of Radical Cations with 11pi Electron Framework" Chem.Lett.in press.

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1994 Final Research Report Summary
  • [Publications] Ryu Sato, Tetsuya Ohyama, and Satoshi Ogawa: "Efficient Synthesis and Biological Properties of New Benzopentathiepins" Heterocycles. in press.

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1994 Final Research Report Summary
  • [Publications] Satoshi Ogawa, Mitsugu Saito, Michiko Ogasawara, and Ryu Sato: "Preparation and Multi-Nuclear NMR Study of New Benzodichalcogenaphospholes" Heterocycles. in press.

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1994 Final Research Report Summary
  • [Publications] Ryu Sato: "Ammonium Sulfide" Encyclopedia Reagent Org.Synth.in press.

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1994 Final Research Report Summary
  • [Publications] Ryu Sato: "Boron Trisulfide" Encyclopedia Reagent Org.Synth.in press.

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1994 Final Research Report Summary
  • [Publications] Satoshi Ogawa,Naoki Yomoji,Shi-ichi Chida,and Ryu Sato: "An Effective and Selective Synthesis of Sterically Crowded Benzotrithioles from Benzodithiastannoles via Benzotrithiole-2-oxides" Chem.Lett.507-510 (1994)

    • Related Report
      1994 Annual Research Report
  • [Publications] Ryu Sato,Tetsuya Ohyama,and Satoshi Ogawa: "Efficient Synthesis and Biological Properties of New Benzopen tathiepins" Heterocycles. (in press).

    • Related Report
      1994 Annual Research Report
  • [Publications] Satoshi Ogawa,Sachiko Ohara,Yasushi Kawai,and Ryu Sato: "SYNTHESIS AND MOLECULAR STRUCTURE OF 3,4,13,14-TETRASELENATRICYCLO-[14.4.0.0^<6,11>]ICOSA-1(16),6,8,10,17,19-HEXAENE" Heterocycles. 38. 491-494 (1994)

    • Related Report
      1993 Annual Research Report

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Published: 1993-04-01   Modified: 2016-04-21  

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