2-(p-trifluoromethoxyanilino)ethanesulphonyl fluoride | 130997-80-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 2-(p-trifluoromethoxyanilino)ethanesulphonyl fluoride
• 英文别名: 2-[4-(trifluoromethoxy)anilino]ethanesulfonyl fluoride
• CAS: 130997-80-7
• 化学式: C₉H₉F₄NO₃S
• 分子量: 287.235
• InChiKey: VDBLJLFELZOOTJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  63.8
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  2-(p-trifluoromethoxyanilino)ethanesulphonyl fluoride 在 ammonium hydroxide 作用下， 以 丙酮 为溶剂， 反应 1.0h， 以64%的产率得到2-(p-trifluoromethoxyanilino)ethanesulphonamide
  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：

  乙烯磺酰氟 、 对三氟甲氧基苯胺 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 以75%的产率得到2-(p-trifluoromethoxyanilino)ethanesulphonyl fluoride
  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

• 2-imino-6-polyfluoroalkoxybenzothiazole derivatives, and pharamaceutical
  申请人：Rhone-Poulenc Sante

  公开号：US04980356A1

  公开（公告）日：1990-12-25

  Compounds of formula: ##STR1## and their salts, in which R.sub.1 represents polyfluoroalkoxy, and R.sub.2 represents alkyl, alkenyl (3-6 C), [cycloalkyl (3-6 C)]-alkyl, carbamoylalkyl, dialkylcarbamoylalkyl, acylaminoalkyl, phenylthioalkyl, hydroxyalkyl, cyanoalkyl, sulphamoylethyl, N-alkylsulphamoylethyl, pyridylthioalkyl, pyridiylalkylthioalkyl, pyridylsulphinylalkyl, alkynyl (3-6 C), phenylsulphinylalkyl, halophenylthioalkyl, (2,2,2-trifluoroethylthio)alkyl, 2-dialkylaminopropyl, pyrimidinylsulphinylalkyl, pyridylalkylsulphinylalkyl, halophenylsulphinylalkyl or (2,2,2-trifluoroethylsulphinyl)alkyl are useful in the treatment of medical conditions associated with the effects of glutamate.

  式为：##STR1##及其盐，其中R.sub.1代表多氟烷氧基，R.sub.2代表烷基，烯基（3-6 C），[环烷基（3-6 C）]-烷基，氨基甲酰烷基，二烷基氨基甲酰烷基，酰胺基烷基，苯硫基烷基，羟基烷基，氰基烷基，磺酰乙基，N-烷基磺酰乙基，吡啶硫基烷基，吡啶烷基硫基烷基，吡啶磺氧基烷基，炔基（3-6 C），苯基磺氧基烷基，卤代苯基硫基烷基，（2,2,2-三氟乙硫基）烷基，2-二烷基氨基丙基，嘧啶磺氧基烷基，吡啶烷基磺氧基烷基，卤代苯基磺氧基烷基或（2,2,2-三氟乙磺氧基）烷基在治疗与谷氨酸作用有关的医疗状况中是有用的。
• US4980356A
  申请人：——

  公开号：US4980356A

  公开（公告）日：1990-12-25
• US5026717A
  申请人：——

  公开号：US5026717A

  公开（公告）日：1991-06-25
• 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.