2-(2-Imino-6-trifluoromethoxy-3-benzothiazolinyl)ethanol | 133783-55-8

• 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-(2-Imino-6-trifluoromethoxy-3-benzothiazolinyl)ethanol
• 英文别名: 3-(2-hydroxyethyl)-2-imino-6-trifluoromethoxybenzothiazoline；2-[2-imino-6-(trifluoromethoxy)-1,3-benzothiazol-3-yl]ethanol
• CAS: 133783-55-8
• 化学式: C₁₀H₉F₃N₂O₂S
• 分子量: 278.255
• InChiKey: SODICPUNWKPVDQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  18
• 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：
  81.8
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  2-(2-Imino-6-trifluoromethoxy-3-benzothiazolinyl)ethanol 在 吡啶 、 碳酸氢钠 、 potassium carbonate 、 三乙胺 作用下， 以 甲醇 、 乙醇 、 N,N-二甲基甲酰胺 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 溴 、 溶剂黄146 作用下， 以 丁酮 为溶剂， 反应 45.0h， 生成 2-(2-Imino-6-trifluoromethoxy-3-benzothiazolinyl)ethanol
  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。
• 2-imino-3-alkylbenzothiazoline derivatives bearing a heterocyclic
  申请人：Rhone Poulenc Rorer, S.A.

  公开号：US05260297A1

  公开（公告）日：1993-11-09

  Compounds of formula: ##STR1## in which R.sub.1 represents a substituted 1-piperazinyl, substituted 1,2,3,6-tetrahydro-1-pyridyl or substituted piperidino radical, R.sub.2 represents a polyfluoroalkoxy or a polyfluoroalkyl radical and n is equal to 2 or 3, the salts of these compounds with an acid, processes for preparing them and medicinal products containing them.

  化合物的公式为：##STR1## 其中R.sub.1代表取代的1-哌嗪基，取代的1,2,3,6-四氢-1-吡啶基或取代的哌啶基，R.sub.2代表多氟烷氧基或多氟烷基，n等于2或3，这些化合物的酸盐，制备它们的过程以及含有它们的药物制剂。
• 2-iminobenzothiazoline derivatives, their preparation and pharmaceutical
  申请人：Rhone-Poulenc Sante

  公开号：US05008280A1

  公开（公告）日：1991-04-16

  Compounds of the formula: ##STR1## in which - R.sub.1 denotes a polyfluoroalkoxy or polyfluoroalkyl radical, and - R.sub.2 denotes either a chain --CH.sub.2 --(CH(R.sub.4)).sub.n --R.sub.3, in which R.sub.3 denotes a dialkylamino, piperidino, 1-pyrrolidinyl, mercapto, acylthio, alkylthio, alkylsulphinyl or alkylsulphonyl radical, R.sub.4 denotes a hydrogen atom or an alkyl radical and n is equal to 0 or 1, or a residue of formula: ##STR2## the said alkyl and alkoxy radicals and portions containing 1 to 4 carbon atoms each in a straight or branched chain and said the acyl portions containing 2 to 4 carbon atoms each, and the salts of these compounds, are useful in the treatment of diseases in which glutamate is implicated.

  化合物的公式为：##STR1## 其中 - R.sub.1表示多氟烷氧基或多氟烷基基团，而 - R.sub.2则表示链 -CH.sub.2--(CH(R.sub.4)).sub.n--R.sub.3，其中R.sub.3表示二烷基氨基，哌啶基，1-吡咯烷基，巯基，酰硫基，烷基硫基，烷基磺酰基基团，R.sub.4表示氢原子或烷基基团，n等于0或1，或者为公式的残基：##STR2## 所述的烷基和烷氧基基团以及含有1至4个碳原子的直链或支链部分，以及含有2至4个碳原子的酰基部分和这些化合物的盐，在涉及谷氨酸的疾病治疗中是有用的。
• JIMONET, PATRICK;GUEREMY, CLAUDE;MIGNANI, SERGE
  作者：JIMONET, PATRICK、GUEREMY, CLAUDE、MIGNANI, SERGE

  DOI：——

  日期：——
• US4980356A
  申请人：——

  公开号：US4980356A

  公开（公告）日：1990-12-25