2,2,2-Trifluoro-N-[3-[2-(4-phenyl-piperazin-1-yl)-ethyl]-6-trifluoromethoxy-3H-benzothiazol-(2Z)-ylidene]-acetamide | 732218-64-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪烷类
• 英文名称: 2,2,2-Trifluoro-N-[3-[2-(4-phenyl-piperazin-1-yl)-ethyl]-6-trifluoromethoxy-3H-benzothiazol-(2Z)-ylidene]-acetamide
• 英文别名: 2,2,2-trifluoro-N-[3-[2-(4-phenylpiperazin-1-yl)ethyl]-6-(trifluoromethoxy)-1,3-benzothiazol-2-ylidene]acetamide
• CAS: 732218-64-3
• 化学式: C₂₂H₂₀F₆N₄O₂S
• 分子量: 518.483
• InChiKey: FIIOHNQZQQQWRY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  35
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  73.7
• 氢给体数：
  0
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  2,2,2-Trifluoro-N-[3-[2-(4-phenyl-piperazin-1-yl)-ethyl]-6-trifluoromethoxy-3H-benzothiazol-(2Z)-ylidene]-acetamide 在 potassium carbonate 作用下， 以 甲醇 为溶剂， 反应 5.0h， 生成 2-imino-3-(2-(4-phenylpiperazinyl)ethyl)-6-trifluoromethoxybenzothiazoline
  参考文献：
  名称：

  Riluzole Series. Synthesis and in Vivo “Antiglutamate” Activity of 6-Substituted-2-benzothiazolamines and 3-Substituted-2-imino-benzothiazolines

  摘要：

  Two series of analogues of riluzole, a blocker of excitatory amino acid mediated neurotransmission, have been synthesized: monosubstituted 2-benzothiazolamines and 3-substituted derivatives. Of all the compounds prepared in the first series, only 2-benzothiazolamines bearing alkyl, polyfluoroalkyl, or polyfluoroalkoxy substituents in the 6-position showed potent anticonvulsant activity against administration of glutamic acid in rats. The most active compounds displaying in vivo "antiglutamate" activity were the 6-OCF3 (riluzole), 6-OCF2CF3, 6-CF3, and 6-CF2CF3 substituted derivatives with ED50 values between 2.5 and 3.2 mg/kg i.p. Among the second series of variously substituted benzothiazolines, compounds as active as riluzole or up to 3 times more potent were identified in two series: benzothiazolines bearing a beta-dialkylaminoethyl moiety and compounds with an alkylthioalkyl chain and their corresponding sulfoxides and sulfones. The most potent derivatives were 2-imino-3-(2-methylthio)- and 2-imino-3-(2-methylsulfinyl)-ethyl-6-trifluoromethoxybenzothiazlines (61 and 64, ED50 = 10 and 1.1 mg/kg i.p., respectively). In addition, intraperitoneal administration of some of the best benzothiazolines protected mice from mortality produced by hypobaric hypoxia.

  DOI：

  10.1021/jm980202u
• 作为产物：
  描述：

  对三氟甲氧基苯胺 在 吡啶 、 溴 、 碳酸氢钠 、 溶剂黄146 、 三乙胺 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 、 丁酮 为溶剂， 反应 45.0h， 生成 2,2,2-Trifluoro-N-[3-[2-(4-phenyl-piperazin-1-yl)-ethyl]-6-trifluoromethoxy-3H-benzothiazol-(2Z)-ylidene]-acetamide
  参考文献：
  名称：

  Riluzole Series. Synthesis and in Vivo “Antiglutamate” Activity of 6-Substituted-2-benzothiazolamines and 3-Substituted-2-imino-benzothiazolines

  摘要：

  Two series of analogues of riluzole, a blocker of excitatory amino acid mediated neurotransmission, have been synthesized: monosubstituted 2-benzothiazolamines and 3-substituted derivatives. Of all the compounds prepared in the first series, only 2-benzothiazolamines bearing alkyl, polyfluoroalkyl, or polyfluoroalkoxy substituents in the 6-position showed potent anticonvulsant activity against administration of glutamic acid in rats. The most active compounds displaying in vivo "antiglutamate" activity were the 6-OCF3 (riluzole), 6-OCF2CF3, 6-CF3, and 6-CF2CF3 substituted derivatives with ED50 values between 2.5 and 3.2 mg/kg i.p. Among the second series of variously substituted benzothiazolines, compounds as active as riluzole or up to 3 times more potent were identified in two series: benzothiazolines bearing a beta-dialkylaminoethyl moiety and compounds with an alkylthioalkyl chain and their corresponding sulfoxides and sulfones. The most potent derivatives were 2-imino-3-(2-methylthio)- and 2-imino-3-(2-methylsulfinyl)-ethyl-6-trifluoromethoxybenzothiazlines (61 and 64, ED50 = 10 and 1.1 mg/kg i.p., respectively). In addition, intraperitoneal administration of some of the best benzothiazolines protected mice from mortality produced by hypobaric hypoxia.

  DOI：

  10.1021/jm980202u

文献信息

• Riluzole Series. Synthesis and in Vivo “Antiglutamate” Activity of 6-Substituted-2-benzothiazolamines and 3-Substituted-2-imino-benzothiazolines
  作者：Patrick Jimonet、François Audiau、Michel Barreau、Jean-Charles Blanchard、Alain Boireau、Yvette Bour、Marie-Annick Coléno、Adam Doble、Gilles Doerflinger、Claudine Do Huu、Marie-Hélène Donat、Jean Marie Duchesne、Pierre Ganil、Claude Guérémy、Eliane Honoré,、Bernard Just、Roselyne Kerphirique、Sylvie Gontier、Philippe Hubert、Pierre M. Laduron、Joseph Le Blevec、Mireille Meunier、Jean-Marie Miquet、Conception Nemecek、Martine Pasquet、Odile Piot、Jeremy Pratt、Jean Rataud、Michel Reibaud、Jean-Marie Stutzmann、Serge Mignani

  DOI：10.1021/jm980202u

  日期：1999.7.1

  Two series of analogues of riluzole, a blocker of excitatory amino acid mediated neurotransmission, have been synthesized: monosubstituted 2-benzothiazolamines and 3-substituted derivatives. Of all the compounds prepared in the first series, only 2-benzothiazolamines bearing alkyl, polyfluoroalkyl, or polyfluoroalkoxy substituents in the 6-position showed potent anticonvulsant activity against administration of glutamic acid in rats. The most active compounds displaying in vivo "antiglutamate" activity were the 6-OCF3 (riluzole), 6-OCF2CF3, 6-CF3, and 6-CF2CF3 substituted derivatives with ED50 values between 2.5 and 3.2 mg/kg i.p. Among the second series of variously substituted benzothiazolines, compounds as active as riluzole or up to 3 times more potent were identified in two series: benzothiazolines bearing a beta-dialkylaminoethyl moiety and compounds with an alkylthioalkyl chain and their corresponding sulfoxides and sulfones. The most potent derivatives were 2-imino-3-(2-methylthio)- and 2-imino-3-(2-methylsulfinyl)-ethyl-6-trifluoromethoxybenzothiazlines (61 and 64, ED50 = 10 and 1.1 mg/kg i.p., respectively). In addition, intraperitoneal administration of some of the best benzothiazolines protected mice from mortality produced by hypobaric hypoxia.