3-fluorobenzoic acid (6-trifluoromethoxy-3-methyl-3H-benzothiazol-2-ylidine)hydrazide | 1203461-82-8

• 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: 3-fluorobenzoic acid (6-trifluoromethoxy-3-methyl-3H-benzothiazol-2-ylidine)hydrazide
• 英文别名: 3-fluoro-N-[[3-methyl-6-(trifluoromethoxy)-1,3-benzothiazol-2-ylidene]amino]benzamide
• CAS: 1203461-82-8
• 化学式: C₁₆H₁₁F₄N₃O₂S
• 分子量: 385.342
• InChiKey: LLKUTDWMTVLVHZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.52
• 重原子数：
  26.0
• 可旋转键数：
  3.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  55.62
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为产物：
  描述：

  (6-trifluoromethoxy-3-methyl-3H-benzothiazol-2-ylidine)hydrazine 、 间氟苯甲酰氯 在 potassium carbonate 作用下， 以 水 、 乙腈 为溶剂， 反应 1.0h， 生成 3-fluorobenzoic acid (6-trifluoromethoxy-3-methyl-3H-benzothiazol-2-ylidine)hydrazide
  参考文献：
  名称：

  Novel KCNQ2/Q3 Agonists as Potential Therapeutics for Epilepsy and Neuropathic Pain

  摘要：

  Current drugs for the treatment of seizure disorders, although effective in many patients, still suffer from a number of failures and are not effective in some forms of resistant epilepsies. Historically, many of these drugs have multiple mechanisms of action including calcium and sodium channel blockade as well as GABAergic activity and thus a number of associated side effects. Modulation of the M-current through opening of KCNQ channels has been proposed as a way to attenuate neuroexcitability and have a therapeutic benefit for the treatment Of seizure disorders. Therefore, as part Of our program to identify new treatments for epilepsy, we set out to identify agonists of KCNQ channels. High throughput screening of our corporate collection led to the identification of 1, adamantane-1-carboxylic acid (3-methyl-3H-benzothiazol-2-ylidine) hydrazide, a potent KCNQ2/Q3 agonist. Herein, we describe the syntheses and structure-activity relationships of analogues of I its well as their in vivo activity in animal models of epilepsy and neuropathic pain.

  DOI：

  10.1021/jm901497b

文献信息

• Novel KCNQ2/Q3 Agonists as Potential Therapeutics for Epilepsy and Neuropathic Pain
  作者：Paul C. Fritch、Grant McNaughton-Smith、George S. Amato、James F. Burns、C. Wesley Eargle、Rosemarie Roeloffs、William Harrison、Leslie Jones、Alan D. Wickenden

  DOI：10.1021/jm901497b

  日期：2010.1.28

  Current drugs for the treatment of seizure disorders, although effective in many patients, still suffer from a number of failures and are not effective in some forms of resistant epilepsies. Historically, many of these drugs have multiple mechanisms of action including calcium and sodium channel blockade as well as GABAergic activity and thus a number of associated side effects. Modulation of the M-current through opening of KCNQ channels has been proposed as a way to attenuate neuroexcitability and have a therapeutic benefit for the treatment Of seizure disorders. Therefore, as part Of our program to identify new treatments for epilepsy, we set out to identify agonists of KCNQ channels. High throughput screening of our corporate collection led to the identification of 1, adamantane-1-carboxylic acid (3-methyl-3H-benzothiazol-2-ylidine) hydrazide, a potent KCNQ2/Q3 agonist. Herein, we describe the syntheses and structure-activity relationships of analogues of I its well as their in vivo activity in animal models of epilepsy and neuropathic pain.