Synthesis of Fluorine Analogs of Protoporphyrin Potentially Useful for Diagnosis and Therapy of Cancer. IV.Synthesis of (Trifluorovinyl)vinyl-and (1-Chloro-2,2-difluorovinyl)vinyldeuteroporphyrins

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概要

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• Trifluoro or Chlorodifluoro analogs lf protoporphyrin, the compounds in the title, were synthesized for use in the diagnosis and therapy of cancer. 3-Or 8-acetyldeuteroporphyrin dimethyl esters (2 and 3) were iodinated with iodine in the presence of potassium carbonate to the corresponding iodo compounds (5 and 6). The iodo compounds (5 and 6) were treated with bis(trifluorovinyl)zinc in the presence of tetrakis(triphenylphosphine)-palladium to give trifluorovinyl derivatives (7 and 8) in good yields.Reduction of the acetyl group of 7 and 8 with sodium borohydride afforded the corresponding hydroxyethyl derivatives (9 and 10). Compounds (9 and 10) were dehydrated with methanesulfonyl chloride and triethylamine to give (trifluorovinyl)vinyldeuteroporphyrin dimethyl esters (11 and 12).Treatment of 5 and 6 with bis(1-chloro-2,2-difluorovinyl)zinc in the presence of tetrakis(triphenylphosphine)palladium, followed by similar reactions as above gave (1-chloro-2,2-difluorovinyl)-vinyldeuteroporphyrin dimethyl esters (17 and 18).

• 公益社団法人日本薬学会の論文
• 1999-09-15

著者

• Watanabe K

  School Of Life Science Tokyo University Of Pharmacy And Life Science

• 安藤 章

  Faculty of Pharmaceutical Sciences, Setsunan University

• Ando A

  Faculty Of Pharmaceutical Sciences Setsunan University

• SHIGEOKA Tsuyoshi

  Faculty of Pharmaceutical Sciences

• KUWAHARA Yasuhisa

  Faculty of Pharmaceutical Sciences

• WATANABE Kiyoko

  Faculty of Pharmaceutical Sciences

• SATO Kasuyuki

  Faculty of Pharmaceutical Sciences

• OMOTE Masaaki

  Faculty of Pharmaceutical Sciences

• ANDO Akira

  Faculty of Pharmaceutical Sciences

• KUMADAKI Itsumaro

  Faculty of Pharmaceutical Sciences

• SATO Kazuyuki

  Faculty of Pharmaceutical Sciences, Setsunan University

• Omote M

  Faculty Of Pharmaceutical Sciences Setsunan University

• Kumadaki I

  Faculty Of Pharmaceutical Sciences Setsunan University

• Watanabe Kazuki

  Faculty Of Pharmaceutical Sciences Aomori University

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