2-amino-6-ethyl-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidin-4(3H)-one | 1211468-41-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶并嘧啶类
• 英文名称: 2-amino-6-ethyl-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidin-4(3H)-one
• 英文别名: 2-amino-6-ethyl-3,5,7,8-tetrahydropyrido[4,3-d]pyrimidin-4-one
• CAS: 1211468-41-5
• 化学式: C₉H₁₄N₄O
• mdl: MFCD15203896
• 分子量: 194.236
• InChiKey: IVTCBDJMYOUHST-UHFFFAOYSA-N

物化性质

• 沸点：
  365.7±52.0 °C(Predicted)
• 密度：
  1.45±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.62
• 重原子数：
  14.0
• 可旋转键数：
  1.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.555
• 拓扑面积：
  75.27
• 氢给体数：
  2.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  4-苯氧基苯甲酸 、 2-amino-6-ethyl-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidin-4(3H)-one 在 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 以71%的产率得到N-(6-ethyl-4-hydroxy-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidin-2-yl)-4-phenoxybenzamide
  参考文献：
  名称：

  Discovery of tetrahydropyrido[4,3-d]pyrimidine derivatives for the treatment of neuropathic pain

  摘要：

  A series of tetrahydropyridopyrimidine derivatives were synthesized and evaluated for neurotoxicity and peripheral analgesic activity followed by assessment of antiallodynic and antihyperalgesic potential in two peripheral neuropathic pain models, the chronic constriction injury (CCI) and partial sciatic nerve ligation (PSNL). Compounds (4b and 4d) exhibiting promising efficacies in four behavioral assays of allodynia and hyperalgesia (spontaneous pain, tactile allodynia, cold allodynia and mechanical hyperalgesia) were quantified for their ED50 values (15.12-65.10 mg/kg). Studies carried out to assess the underlying mechanism revealed that the compounds suppressed the inflammatory component of the neuropathic pain and prevented oxidative and nitrosative stress. (C) 2013 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.bioorg.2013.11.007
• 作为产物：
  描述：

  N-乙基-4-哌啶酮 在 sodium hydride 、 potassium carbonate 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 6.0h， 生成 2-amino-6-ethyl-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidin-4(3H)-one
  参考文献：
  名称：

  Discovery of tetrahydropyrido[4,3-d]pyrimidine derivatives for the treatment of neuropathic pain

  摘要：

  A series of tetrahydropyridopyrimidine derivatives were synthesized and evaluated for neurotoxicity and peripheral analgesic activity followed by assessment of antiallodynic and antihyperalgesic potential in two peripheral neuropathic pain models, the chronic constriction injury (CCI) and partial sciatic nerve ligation (PSNL). Compounds (4b and 4d) exhibiting promising efficacies in four behavioral assays of allodynia and hyperalgesia (spontaneous pain, tactile allodynia, cold allodynia and mechanical hyperalgesia) were quantified for their ED50 values (15.12-65.10 mg/kg). Studies carried out to assess the underlying mechanism revealed that the compounds suppressed the inflammatory component of the neuropathic pain and prevented oxidative and nitrosative stress. (C) 2013 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.bioorg.2013.11.007