adamantane-1-carboxylic acid (3-methyl-3H-benzoxazol-2-ylidine)hydrazide | 1203461-72-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并恶唑类
• 英文名称: adamantane-1-carboxylic acid (3-methyl-3H-benzoxazol-2-ylidine)hydrazide
• 英文别名: N-[(3-methyl-1,3-benzoxazol-2-ylidene)amino]adamantane-1-carboxamide
• CAS: 1203461-72-6
• 化学式: C₁₉H₂₃N₃O₂
• 分子量: 325.411
• InChiKey: PZHFNGCPUBXBQI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.92
• 重原子数：
  24.0
• 可旋转键数：
  2.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  59.53
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为产物：
  描述：

  3-甲基-1,3-苯并噁唑-2(3H)-硫酮 、 金刚烷-1-甲酰肼 、 三氟甲烷磺酸甲酯 在 三乙胺 作用下， 以 1,2-二氯乙烷 、 乙醇 为溶剂， 反应 8.0h， 以268 mg的产率得到adamantane-1-carboxylic acid (3-methyl-3H-benzoxazol-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.