2-(N-ethylamine)-6-trifluoromethoxy-benzothiazole | 133840-99-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻唑类
• 英文名称: 2-(N-ethylamine)-6-trifluoromethoxy-benzothiazole
• 英文别名: 2-Ethylamino-6-trifluoromethoxybenzothiazole；N-ethyl-6-(trifluoromethoxy)-1,3-benzothiazol-2-amine
• CAS: 133840-99-0
• 化学式: C₁₀H₉F₃N₂OS
• 分子量: 262.255
• InChiKey: WHIDHFSHJHEDDG-UHFFFAOYSA-N

物化性质

• 沸点：
  288.3±50.0 °C(Predicted)
• 密度：
  1.436±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  62.4
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  2-氯乙基甲基硫醚 、 2-(N-ethylamine)-6-trifluoromethoxy-benzothiazole 以 丁酮 为溶剂， 反应 48.0h， 生成 2-ethylimino-3-(2-methylthioethyl)-6-trifluoromethoxy-benzothiazoline hydrochloride
  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 氯化亚砜 、 溴 、 溶剂黄146 、 肼 作用下， 以 水 为溶剂， 反应 45.0h， 生成 2-(N-ethylamine)-6-trifluoromethoxy-benzothiazole
  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

• Synthesis, crystal structure, and antinociceptive effects of some new riluzole derivatives
  作者：Xiang-Long Wu、Liu Liu、You-Jia Li、Jie Luo、Dong-Wei Gai、Ting-Li Lu、Qi-Bing Mei

  DOI：10.1007/s00044-018-2154-4

  日期：2018.5

  riluzole respectively. The structures of compounds were confirmed by means of elemental analysis, IR, 1H NMR, and 13C NMR. The synthetic route was optimized and four novel crystals were obtained by recrystallization. This study investigated the antinociceptive activity of some N-alkylated derivatives of riluzole by hot plate test in mice. The relationship between antinociceptive activity and the doses of

  合成了九种利鲁唑的N-烷基化衍生物，以获得具有潜在抗伤害感受活性的新化合物。首先将利鲁唑转化为（6-三氟甲氧基-苯并噻唑-2-基）-肼，然后用SOCl 2氯化，得到2-氯-6-三氟甲氧基-苯并噻唑。该中间产物用九种烷基胺处理，分别得到利鲁唑的N-烷基化衍生物。通过元素分析，IR，1 H NMR和13确认化合物的结构1 H NMR。优化了合成路线，并通过重结晶获得了四个新颖的​​晶体。这项研究通过热板实验在小鼠中研究了利鲁唑的某些N-烷基化衍生物的抗伤害感受活性。研究了抗伤害感受活性与4b，4c，4h，4g和利鲁唑剂量之间的关系。与对照组（0 mg / kg）相比，化合物4b和4h的作用显着增加（分别为13.78±2.89 s，12.89±2.94 s）。化合物4c在小鼠停留在热板上的时间显示出极大的显着增加（18.07±3.08 s）。化合物4b，4c，与空白溶剂组相比，4h增加了潜伏时间
• 2-alkyliminobenzothiazoline derivatives, processes for preparing them
  申请人：Rhone-Poulenc Sante

  公开号：US05068238A1

  公开（公告）日：1991-11-26

  Compounds of formula: ##STR1## R.sub.1 represents a polyfluoroalkoxy radical, R.sub.2 represents an alkylthioalkyl, alkylsulphinylalkyl or alkylsulphonylalkyl radical, and R.sub.3 represents an alkyl radical, as well as the salts of these compounds with an inorganic or organic acid, processes for preparing them and medicinal products containing them.

  化合物的化学式为：## STR1 ##其中，R.sub.1代表聚氟烷氧基基团，R.sub.2代表烷基硫醇基团、烷基亚磺酰基团或烷基磺酰基团，R.sub.3代表烷基基团，以及这些化合物与无机或有机酸的盐，制备它们的过程以及包含它们的药物制品。
• US5068238A
  申请人：——

  公开号：US5068238A

  公开（公告）日：1991-11-26
• 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.