ethyl 3,5-diamino-1,2,4-triazine-6-carboxylate | 1620495-72-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 三嗪类
• 英文名称: ethyl 3,5-diamino-1,2,4-triazine-6-carboxylate
• CAS: 1620495-72-8
• 化学式: C₆H₉N₅O₂
• 分子量: 183.17
• InChiKey: YKDPJPPCAZBDCC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.79
• 重原子数：
  13.0
• 可旋转键数：
  2.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  117.01
• 氢给体数：
  2.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  6-bromo-3-(pyrrolidin-2-yl)benzo[d]isoxazole 、 ethyl 3,5-diamino-1,2,4-triazine-6-carboxylate 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 反应 48.0h， 以52%的产率得到(2-(6-bromobenzo[d]isoxazol-3-yl)pyrrolidin-1-yl)(3,5-diamino-1,2,4-triazin-6-yl)methanone
  参考文献：
  名称：

  Design and synthesis of (5-amino-1, 2, 4-triazin-6-yl)(2-(benzo[d] isoxazol-3-yl) pyrrolidin-1-yl)methanone derivatives as sodium channel blocker and anticonvulsant agents

  摘要：

  A series of novel (5-amino-3-substituted-1, 2, 4-triazin-6-yl) (2-(6-halo-substituted benzo[d]isoxazol-3-yl) pyrrolidin-1-yl) methanone 5a-5r was synthesized. Their anticonvulsant activities were evaluated by the maximal electroshock (MES) test and neurotoxicity was evaluated by the rotorod test. The MES test showed that (5-amino-3-phenyl-1, 2, 4-triazin-6-yl)(2-(6-fluorobenzo[d]isoxazol-3-yl) pyrrolidin-1-yl) methanone 5c was found to be the most potent compound with ED50 value of 6.20 mg/kg (oral/rat) and a protective index (PI = ED50/TD50) value of >48.38, which was much higher than the PI of the reference drug phenytoin. To explain the possible mechanism of action of selected derivatives 5 b, 5 c, 5 i and 5 o, their influence on sodium channel was evaluated in vitro.

  DOI：

  10.3109/14756366.2013.815177
• 作为产物：
  描述：

  ethyl 3-amino-2-hydroxy-3-oxopropanoate 在 copper(II) acetate monohydrate 作用下， 以 乙醇 为溶剂， 反应 3.0h， 生成 ethyl 3,5-diamino-1,2,4-triazine-6-carboxylate
  参考文献：
  名称：

  Design and synthesis of (5-amino-1, 2, 4-triazin-6-yl)(2-(benzo[d] isoxazol-3-yl) pyrrolidin-1-yl)methanone derivatives as sodium channel blocker and anticonvulsant agents

  摘要：

  A series of novel (5-amino-3-substituted-1, 2, 4-triazin-6-yl) (2-(6-halo-substituted benzo[d]isoxazol-3-yl) pyrrolidin-1-yl) methanone 5a-5r was synthesized. Their anticonvulsant activities were evaluated by the maximal electroshock (MES) test and neurotoxicity was evaluated by the rotorod test. The MES test showed that (5-amino-3-phenyl-1, 2, 4-triazin-6-yl)(2-(6-fluorobenzo[d]isoxazol-3-yl) pyrrolidin-1-yl) methanone 5c was found to be the most potent compound with ED50 value of 6.20 mg/kg (oral/rat) and a protective index (PI = ED50/TD50) value of >48.38, which was much higher than the PI of the reference drug phenytoin. To explain the possible mechanism of action of selected derivatives 5 b, 5 c, 5 i and 5 o, their influence on sodium channel was evaluated in vitro.

  DOI：

  10.3109/14756366.2013.815177