2-亚肼基-6-(三氟甲氧基)-2,3-二氢苯并[d]噻唑 | 133840-98-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻唑类
• 中文名称: 2-亚肼基-6-(三氟甲氧基)-2,3-二氢苯并[d]噻唑
• 英文名称: 2-hydrazinyl-6-(trifluoromethoxy)benzo[d]thiazole
• 英文别名: 2-Hydrazono-6-(trifluoromethoxy)-2,3-dihydrobenzo[d]thiazole；[6-(trifluoromethoxy)-1,3-benzothiazol-2-yl]hydrazine
• CAS: 133840-98-9
• 化学式: C₈H₆F₃N₃OS
• 分子量: 249.216
• InChiKey: DYZRKRXUAGGAPE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  88.4
• 氢给体数：
  2
• 氢受体数：
  8

安全信息

• 海关编码：
  2934200090

反应信息

• 作为反应物：
  描述：

  2-亚肼基-6-(三氟甲氧基)-2,3-二氢苯并[d]噻唑 在 氯化亚砜 、 硫酸 、 sodium methylate 、 硫脲 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 67.0h， 生成 3-(2-Methylsulfanyl-ethyl)-6-trifluoromethoxy-3H-benzothiazol-2-one
  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 、 肼 作用下， 反应 21.0h， 生成 2-亚肼基-6-(三氟甲氧基)-2,3-二氢苯并[d]噻唑
  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

• SUBSTITUTED DIHYDROPYRAZOLONES AND USE THEREOF AS HIF-PROLYL-4 -HYDROXYLASE INHIBITORS
  申请人：Thede Kai

  公开号：US20120264704A1

  公开（公告）日：2012-10-18

  The present application relates to novel substituted dihydropyrazolone derivatives, processes for their preparation, their use for treatment and/or prophylaxis of diseases and their use for the preparation of medicaments for treatment and/or prophylaxis of diseases, in particular cardiovascular and hematological diseases and kidney diseases, and for promoting wound healing.

  本申请涉及新颖的取代二氢吡唑酮衍生物，其制备方法，其用于治疗和/或预防疾病的用途，以及用于制备治疗和/或预防疾病的药物，特别是心血管和血液病以及肾脏疾病，并促进伤口愈合。
• 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
• Propargyl-trifluoromethoxy-amino-benzothiazole derivatives
  申请人：——

  公开号：US20040176430A1

  公开（公告）日：2004-09-09

  The subject invention provides compounds having the structure: 1 wherein R 1 is present or absent, and when present is H, C 1 -C 6 alkyl, C 1 -C 6 alkynyl, —(CH 2 ) y S(CH 2 ) x CH 3 , C 1 -C 6 aminoalkyl, C 1 -C 6 hydroxyalkyl or —(CH 2 ) n C(═O)(C 6 H 4 )(CH 2 )R 2 ; R 2 is H or C 1 -C 4 alkyl; R 3 is H or C 1 -C 4 alkyl; R 4 is present or absent, and when present is H, C 1 -C 6 alkyl, C 1 -C 6 alkynyl, —(CH 2 ) y S(CH 2 ) x CH 3 , C 1 -C 6 aminoalkyl, C 1 -C 6 hydroxyalkyl or —(CH 2 ) n C(═O)(C 6 H 4 )(CH 2 )R 2 ; wherein n is an integer from 1-6; wherein x is 0 or an integer from 1-5 and y is an integer from 1-5, such that x+y<6; at least one of R 1 or R 4 is present; the dashed line represents a bond between one of the nitrogen atoms and the intervening carbon atom; and any compound is charged when both R 1 and R 4 are present, or any specific enantiomer thereof or any pharmaceutically acceptable salt thereof, and a method for treating a neurologic disorder or multiple sclerosis by administering a therapeutically effective amount any of the compounds.

  本发明提供具有以下结构的化合物： 其中R1存在或不存在，当存在时为H、C1-C6烷基、C1-C6炔基、—(CH2)yS(CH2)xCH3、C1-C6氨基烷基、C1-C6羟基烷基或—(CH2)nC(═O)(C6H4)(CH2)R2；R2为H或C1-C4烷基；R3为H或C1-C4烷基；R4存在或不存在，当存在时为H、C1-C6烷基、C1-C6炔基、—(CH2)yS(CH2)xCH3、C1-C6氨基烷基、C1-C6羟基烷基或—(CH2)nC(═O)(C6H4)(CH2)R2；其中n为1-6的整数；其中x为0或1-5的整数，y为1-5的整数，使得x+y<6；R1或R4中至少有一个存在；虚线表示氮原子和介入碳原子之间的键；当R1和R4同时存在时，任何化合物都带电，或其任何特定对映体或其任何药用盐，以及通过给予任何化合物的治疗有效量来治疗神经系统疾病或多发性硬化的方法。
• Process for the preparation of 2-amino-7-nitrobenzo-thiazoles
  申请人：Rhone-Poulenc Rorer S.A.

  公开号：US05567822A1

  公开（公告）日：1996-10-22

  This invention relates to the process for the preparation of 2-amino 7-nitro benzothiazoles of formula (I) ##STR1## consisting in a) nitrating a derivative of formula (II) ##STR2## and b) reacting the compound of formula (III) ##STR3## so obtained with caustic ammonia.

  这项发明涉及制备2-氨基-7-硝基苯并噻唑的过程，化学式如下：a) 通过对化合物的硝化衍生物进行硝化，化学式如下：b) 用强碱性氨水处理得到的化合物进行反应。
• 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。