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Synthesis of 1,2,4-Triazine Derivatives as Biologically Active Compounds

Research Project

Project/Area Number 61470144
Research Category

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

Allocation TypeSingle-year Grants
Research Field Chemical pharmacy
Research InstitutionTOHOKU UNIVERSITY

Principal Investigator

YAMANAKA Hiroshi  Tohoku University, Professor, 薬学部, 教授 (40004551)

Co-Investigator(Kenkyū-buntansha) NISHIMURA Sumiko  Tohoku University, Research Associates, 薬学部, 教務系技官 (60156106)
SAGI Mataichi  Tohoku University, Research Associates, 薬学部, 教務系技官 (80134005)
KONDO Yoshinori  Tohoku University, Instructor, 薬学部, 助手 (90162122)
KONNO Shoetsu  Tohoku University, Instructor, 薬学部, 助手 (10006348)
SAKAMOTO Takao  Tohoku University, Instructor (KAWAZOE,Yosh), 薬学部, 助手 (00006347)
Project Period (FY) 1986 – 1987
Project Status Completed (Fiscal Year 1987)
Budget Amount *help
¥5,300,000 (Direct Cost: ¥5,300,000)
Fiscal Year 1987: ¥1,000,000 (Direct Cost: ¥1,000,000)
Fiscal Year 1986: ¥4,300,000 (Direct Cost: ¥4,300,000)
KeywordsAlkynyl-1,2,4-triazine / Alkenyl-1,2,4-triazine / Nucleophilic substitution reaction / Antifungal activity / 血小板凝集抑制活性 / 1,2,4-トリアジン / アケチレンクロスカップリング反応 / Wittig反応
Research Abstract

1. Palladium catalyzed cross-coupling reaction of 3- and 5-iodo-1,2,4-triazine (as-triazines) with monosubstituted acetylenes gave the corrsponding alkynyll- as-triazines. The reaction of alkynyl-as-triazines with piperidine followed by the hydrolysis of the resulting enamines gave the acylmethyl-as-triazins.
2. Methyl-diphenyl-as-triazines were treated with chloine to give trichloro- methyl-as-triazines. On treatment with excess of triphenylphosphine, diphenyl-- as-triazinyl)methylenetriphenylphosphoranes were obtained. The condensation of phosphoranes with various aldehydes affored alkenyl-diphenyl-as-triazines.
3. The 3-methylsulfonyl-as-trizaine reacted with ONC-nucleophiles to give 3-substituted as-triazines. Similary, 5-subsituted and 6-substituted as-triazines were synthesized.
4. The all as-triazines synthesized here were evaluated for antifungal activity against Pyricularia oryzae by the disk method. Among them, a series of 3-alkyl- thio-5-aryl-as-triazines were found to have the most potent antifungal activity, and the protective effects were determined by the pot tests.
5. A series of as-triazines were tested for inhibitry activity toward arachidonic acid-induced aggregation of rabbit blood platelets in vitro. The 5,6-diaryl- as-triazines were found to have a potent activity activity as blood platelet aggregation inhibitors.

Report

(2 results)
  • 1987 Final Research Report Summary
  • 1986 Annual Research Report
  • Research Products

    (13 results)

All Other

All Publications (13 results)

  • [Publications] Shoetsu Konno: Chemical and Pharmaceutical Bulletin. 35. 1378-1382 (1987)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1987 Final Research Report Summary
  • [Publications] Hiroshi Yamanaka: Heterocycles. 26. 2853-2856 (1987)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1987 Final Research Report Summary
  • [Publications] Shoetsu Konno: Heterocycles. 26. 3111-3114 (1987)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1987 Final Research Report Summary
  • [Publications] Shoesu Konno: Heterocyles. 26. 3259-3264 (1987)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1987 Final Research Report Summary
  • [Publications] 今野昌悦: 薬学雑誌. 108. 142-149 (1988)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1987 Final Research Report Summary
  • [Publications] Shoetsu Konno: Chemical and Pharmaceutical Bulletin.

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1987 Final Research Report Summary
  • [Publications] Hiroshi Yamanaka: "Reaction of 2,4-Diphenyl-1,3,5-triazine Derivatives with Nucleophiles" Heterocycles. 26. 2853-2856 (1987)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1987 Final Research Report Summary
  • [Publications] Shoetsu Konno: "Addition Reaction of Phenylmagnesium Bromide with 1,2,4-Triazines" Heterocycles. 26. 3111-3114 (1987)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1987 Final Research Report Summary
  • [Publications] Shoetsu Konno: "Synthesis of 5-Substituted 1,2,4-triazines" Heterocycles. 26. 3259-3264 (1987)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1987 Final Research Report Summary
  • [Publications] Shoetsu Konno: "Syntheses of 5-Aryl-1,2,4-triazine Derivatives and Their Antifungal Activities" Yakugaku Zasshi. 108. 142-149 (1988)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1987 Final Research Report Summary
  • [Publications] Shoetsu Konno: "Synthesis of Alkenyl-1,2,4-triazines" Chemical and Pharmaceutical Bulletin. in press.

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1987 Final Research Report Summary
  • [Publications] Shoetsu Konno: Heterocycles. 24. 1243-1246 (1986)

    • Related Report
      1986 Annual Research Report
  • [Publications] Shoetsu Konno: Chemical & Pharmaceutical Bulletin. 35. 1378-1382 (1987)

    • Related Report
      1986 Annual Research Report

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Published: 1987-03-31   Modified: 2016-04-21  

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