2-methylamino-6-trifluoromethoxy-benzothiazole | 133840-97-8

• 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-methylamino-6-trifluoromethoxy-benzothiazole
• 英文别名: N-methyl-6-(trifluoromethoxy)benzo[d]thiazol-2-amine；N-methyl-6-(trifluoromethoxy)-1,3-benzothiazol-2-amine
• CAS: 133840-97-8
• 化学式: C₉H₇F₃N₂OS
• 分子量: 248.229
• InChiKey: LJDUSTGAYBBGSZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.22
• 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-氯乙基乙基硫醚 、 2-methylamino-6-trifluoromethoxy-benzothiazole 以 丁酮 为溶剂， 反应 48.0h， 以50.3%的产率得到3-(2-ethylthioethyl)-2-methylimino-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-methylamino-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

• General and efficient method for direct N-monomethylation of aromatic primary amines with methanol
  作者：Feng Li、Jianjiang Xie、Haixia Shan、Chunlou Sun、Lin Chen

  DOI：10.1039/c2ra21487c

  日期：——

  The direct N-monomethylation of aromatic primary amines, including arylamines, arylsulfonamides and amino-azoles, using methanol as a methylating agent has been accomplished in the presence of a [Cp*IrCl2]2/NaOH system. From both synthetic and environmental points of view, the reaction is highly attractive because of low catalyst loading, broad substrate scope and excellent selectivities.

  芳族伯胺的直接N-单甲基化反应，包括芳胺，芳基磺酰胺和氨基唑甲醇在[Cp * IrCl 2 ] 2 / NaOH体系的存在下已经完成了甲基化。从合成和环境的角度来看，由于催化剂用量低，底物范围宽和选择性好，该反应具有很高的吸引力。
• 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.

  公式化合物：##STR1## 中，R.sub.1代表聚氟烷氧基基团，R.sub.2代表烷基硫基烷基、烷基磺酰基烷基或烷基磺基烷基基团，R.sub.3代表烷基基团，以及这些化合物与无机或有机酸盐，制备它们的方法以及含有它们的药物产品。
• Amine prodrugs of pharmaceutical compounds
  申请人：BIOHAVEN THERAPEUTICS LTD.

  公开号：US11083711B2

  公开（公告）日：2021-08-10

  Disclose are amine prodrugs and methods of synthesis thereof. In particular, the amine prodrug comprises a drug molecule and at least one or more prodrug appendage moieties and the method for synthesis the amine prodrug comprises a step of coupling the drug molecule and at least one or more prodrug appendage moieties. Also disclosed are exemplary riluzole prodrugs and methods of synthesis thereof.

  公开胺原药及其合成方法。特别是，胺原药包括药物分子和至少一个或多个原药附属分子，合成胺原药的方法包括偶联药物分子和至少一个或多个原药附属分子的步骤。还公开了示例性利鲁唑原药及其合成方法。
• [EN] PRODRUGS RILUZOLE AND THEIR METHOD OF USE<br/>[FR] PROMÉDICAMENTS DE RILUZOLE ET LEUR PROCÉDÉ D'UTILISATION
  申请人：BIOHAVEN PHARM HOLDING CO LTD

  公开号：WO2016140878A9

  公开（公告）日：2016-10-20
• JIMONET, PATRICK;NEMECEK, CONCEPTION
  作者：JIMONET, PATRICK、NEMECEK, CONCEPTION

  DOI：——

  日期：——