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Development of New Fluorescence Derivatization Reagents with 6-Aminoquinoxalines

Research Project

Project/Area Number 07651038
Research Category

Grant-in-Aid for Scientific Research (C)

Allocation TypeSingle-year Grants
Section一般
Research Field 有機工業化学
Research InstitutionSeikei University

Principal Investigator

KATOH Akira  Seikei University Industrial Chemistry, Professor, 工学部, 教授 (00167339)

Project Period (FY) 1995 – 1996
Project Status Completed (Fiscal Year 1996)
Budget Amount *help
¥2,100,000 (Direct Cost: ¥2,100,000)
Fiscal Year 1996: ¥1,500,000 (Direct Cost: ¥1,500,000)
Fiscal Year 1995: ¥600,000 (Direct Cost: ¥600,000)
Keywords6-aminoquinoxaline / fluorescence property / fatty acid / fluorescence derivatization reagent / crown ether / high sensitivity / HPLC / detection limit / 6-(アシル)アミノキノキサリン / 量子収率 / アルカリ金属イオン / 飽和脂肪酸 / 6-ニトロキノキサリン / 合成 / 長鎖カルボン酸 / 蛍光誘導体化試薬
Research Abstract

There are trace amounts of bioactive substances such as carboxylic acids, alcohols, and amines in the body. The determination of them is quite significant for elucidation of physiological function, diagnosis of sickness, explication of cause of disease, and medical treatment. Therefore, many fluorescence derivatization reagents have been developed for the determination of these substances by high-performance liquid chromatography (HPLS). In this project, I investigated new fluorescent 6-aminoquinoxalines and their application to fluorescence derivatization reagents for carboxylic acids.
1.2,3-Disubstituted 6-nitroquinoxalines were obtained by treatment of 2,3-dichloro-6-nitroquinoxaline with some nucleophiles such as amine, alcochol, and crown ether in high yields. 2. The catalytic hydrogenation with 10% Pd-C afforded fluorescent 6-aminoquinoxalines. 3.6-Aminoquinoxalines were coupled with long-chain carboxylic acids by means of the dicyclohexylcarbodiimide (DCC)-1-hydroxybenzotriazol (HOBt) method t give the corresponding 6- (acyl) aminoquinoxalines. 4.6- (Acyl) aminoquinoxalines were monitored by reversed phase HPLC equipped with a fluorescence detector (lambdaex 330 nm, lambdaem 395 nm) by using a column packed with a Finepak SIL C_<12>S.5. All the peaks were completely separated within 40 min. 6. The detection limit of these N-acyl derivatives were found to be 1.0 fmol/mul (injection volume).
In conclusion, 2,3-disubstituted 6-aminoquinoxalines have been demonstrated to be applicable to new fluorescence derivatization reagents for the carboxylic acids.

Report

(3 results)
  • 1996 Annual Research Report   Final Research Report Summary
  • 1995 Annual Research Report
  • Research Products

    (25 results)

All Other

All Publications (25 results)

  • [Publications] 加藤明良: "Synthesis of 2,3-Disubstituted 6-Aminoquinoxalines and Their Applcation to New Fluorescence Derivatization Reagents for Carboxylic Acids" Chemistry Letters. 369-370 (1996)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1996 Final Research Report Summary
  • [Publications] 加藤明良: "2,3-位に種々の置換基を持つ6-アミノキノキサリン類の合成と蛍光誘導体化試薬への応用" 第26回複素環化学討論会要旨集. 77-80 (1995)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1996 Final Research Report Summary
  • [Publications] 加藤明良: "クラウン環が結合した6-アミノキノキサリン類の合成と蛍光誘導体化試薬への応用" 日本化学会第70春季年会予稿集. 2. 1120 (1996)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1996 Final Research Report Summary
  • [Publications] 加藤明良: "キノキサリン類の合成、構造解析および蛍光特性" 第27回複素環化学討論会要旨集. 230-233 (1996)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1996 Final Research Report Summary
  • [Publications] 加藤明良: "キノキサリン類の特異な反応及び蛍光誘導体化試薬への応用" 第32回有機合成化学協会新潟シンポジウム要旨集. 83-84 (1996)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1996 Final Research Report Summary
  • [Publications] 加藤明良: "2,3-ジ置換6-(ブロモアセチル)アミノキノキサリン誘導体の合成とその蛍光誘導体化試薬への応用" 日本化学会第72春季年会予稿集. (印刷中).

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1996 Final Research Report Summary
  • [Publications] 加藤明良: "Structural Analysis of N-(ω-phenylalkyl) substituted Quinoxalin-2(1H)-ones and-Thiones" Heterocycles. 44. 357-366 (1997)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1996 Final Research Report Summary
  • [Publications] 加藤明良: "P-置換フェニルエチニル基をもつキノキサリン誘導体の合成とその蛍光誘導体化試薬への応用" 日本化学会第72春季年会予稿集. (印刷中).

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1996 Final Research Report Summary
  • [Publications] 加藤明良: "2,3-ジクロロ-6-ニトロキノキサリンとアミノ酸との反応" 成蹊大学工学研究報告. 32. 57-60 (1995)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1996 Final Research Report Summary
  • [Publications] Akira Katoh: "Synthesis of 6-Aminoquinoxalines Having Various Substituents at C-2 and C-3 Positions and Their Application to Fluorescence Dervatization Reagents" Abstracts for 26th Congress of Heterocyclic Chemistry. 77-80 (1995)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1996 Final Research Report Summary
  • [Publications] Akira Katoh: "Synthesis of 2,3-Disubstituted 6-Aminoquinoxalines and Their Application to New Fluorescence Derivatization Reagents for Carboxylic Acids" Chemistry Lett.369-370 (1996)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1996 Final Research Report Summary
  • [Publications] Akira Katoh: "Synthesis of 6-Aminoquinoxalines Bearing Crown Ether and Their Application to the Fluorescence Derivatization Reagent" Abstracts for 70th Spring Meeting of the Chemical Society of Japan. No2. 1120 (1996)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1996 Final Research Report Summary
  • [Publications] Akira Katoh: "Synthesis, Structural Analysis, and Fluorescent Property of Quinoxalines" Abstracts for 26the Congress of Heterocyclic Chemistry. 230-233 (1996)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1996 Final Research Report Summary
  • [Publications] Akira Katoh: "The Specific Reaction for Quinoxalines and Their Application to Fluorescence Drivatization Reagent" Abstracts for 32th Symposium of the Synthetic Organic Chemistry (Niigata). 83-84 (1996)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1996 Final Research Report Summary
  • [Publications] Akira Katoh: "Structural Analysis of N- (omega-Phenylalkyl) substituted Quinoxaline-2 (1H) -ones and-Thiones" Heterocycles. 44. 357-366 (1997)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1996 Final Research Report Summary
  • [Publications] Akira Katoh: "Syntesis of 2,3-Disubstituted 6- (Bromoacetyl) aminoquinoxaline Derivatives and Their Application to the Fluorescence Derivatiztion Reagent" Abstracts for 72th Spring Meeting of Chemical Society of Japan. (in press.).

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1996 Final Research Report Summary
  • [Publications] Akira Katoh: "Synthesis of Quinoxaline Derivatives Bearing p-Substituted Phenylethynyl Group and Their Application to Fluorescence Derivatization Reagent" Abstracts for 72th Spring Meering of the Chemical Society of Japan. (in press.).

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1996 Final Research Report Summary
  • [Publications] 加藤明良: "クラウン環が結合した6-アミノキノキサリン類の合成と蛍光誘導体化試薬への応用" 日本化学会第70春季年会予稿集. 2. 1120- (1996)

    • Related Report
      1996 Annual Research Report
  • [Publications] 加藤明良: "キノキサリン類の合成、構造解析および蛍光特性" 第27会複素環化学討論会要旨集. 230-233 (1996)

    • Related Report
      1996 Annual Research Report
  • [Publications] 加藤明良: "キノキサリン類の特異な反応及び蛍光誘導体化試薬への応用" 第32回有機合成化学協会新潟シンポジウム要旨集. 83-84 (1996)

    • Related Report
      1996 Annual Research Report
  • [Publications] 加藤明良: "Structural Aanalysis of N-(ω-Phenylalkyl) substituted Quinaxalin-Z (IH)-ones and-Thiones" Heterocycles. 44. 357-366 (1997)

    • Related Report
      1996 Annual Research Report
  • [Publications] 加藤明良: "2,3-ジ置換6-(ブロモアセチル)アミノキノキサリン誘導体の合成とその蛍光誘導体化試薬への応用" 日本化学会第72春季年会予稿集. (印刷中).

    • Related Report
      1996 Annual Research Report
  • [Publications] 加藤明良: "p-置換フェニルエチニル基をもつキノキサリン誘導体の合成とその蛍光誘導体化試薬への応用" 日本化学会第72春季年会予稿集. (印刷中).

    • Related Report
      1996 Annual Research Report
  • [Publications] 加藤明良: "2,3-ジクロロ-6-ニトロキノキサリンとアミノ酸との反応" 成蹊大学工学研究報告. 32. 57-60 (1995)

    • Related Report
      1995 Annual Research Report
  • [Publications] 加藤明良: "Synthesis of 2,3-Disubstituted 6-Aminoquinoxalines and Their Application to New Fluorescence Deriratigation Reagents for Carboxylic Acids" Chemistry Letters. (印刷中). (1996)

    • Related Report
      1995 Annual Research Report

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Published: 1995-04-01   Modified: 2016-04-21  

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