Toluene-4-sulfonic acid 3-{2-[(Z)-2,2,2-trifluoro-acetylimino]-6-trifluoromethoxy-benzothiazol-3-yl}-propyl ester | 133783-59-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: Toluene-4-sulfonic acid 3-{2-[(Z)-2,2,2-trifluoro-acetylimino]-6-trifluoromethoxy-benzothiazol-3-yl}-propyl ester
• 英文别名: 3-(2-Trifluoroacetylimino-6-trifluoromethoxy-3-benzothiazolinyl)propyl p-toluenesulphonate；3-[2-(2,2,2-trifluoroacetyl)imino-6-(trifluoromethoxy)-1,3-benzothiazol-3-yl]propyl 4-methylbenzenesulfonate
• CAS: 133783-59-2
• 化学式: C₂₀H₁₆F₆N₂O₅S₂
• 分子量: 542.48
• InChiKey: IZKGWIVZPDYOBV-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：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  119
• 氢给体数：
  0
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  Toluene-4-sulfonic acid 3-{2-[(Z)-2,2,2-trifluoro-acetylimino]-6-trifluoromethoxy-benzothiazol-3-yl}-propyl ester 在 碳酸氢钠 、 potassium carbonate 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 5.0h， 生成 2-imino-3-(3-methylthiopropyl)-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 、 溶剂黄146 、 三乙胺 作用下， 以 乙醇 、 丁酮 为溶剂， 反应 45.0h， 生成 Toluene-4-sulfonic acid 3-{2-[(Z)-2,2,2-trifluoro-acetylimino]-6-trifluoromethoxy-benzothiazol-3-yl}-propyl ester
  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

• 3-(3-alkylthiopropyl)benzothiazoline derivatives, their preparation and
  申请人：Rhone-Poulenc Rorer Pharmaceuticals Inc.

  公开号：US05240948A1

  公开（公告）日：1993-08-31

  Compounds of formula: ##STR1## in which R.sub.1 represents a polyfluoroalkoxy radical and R.sub.2 represents an alkylthio, alkylsulphinyl or alkylsulphonyl radical, their salts, their preparation and the medicaments containing them.

  化合物的公式为：##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，它们的盐，它们的制备方法以及含有它们的药物。