6-{3-[4-(3-Chloro-phenyl)-piperazin-1-yl]-propyl}-3,4-dimethyl-6H-isoxazolo[3,4-d]pyridazin-7-one | 502135-06-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪烷类
• 英文名称: 6-{3-[4-(3-Chloro-phenyl)-piperazin-1-yl]-propyl}-3,4-dimethyl-6H-isoxazolo[3,4-d]pyridazin-7-one
• 英文别名: 6-[3-[4-(3-Chlorophenyl)piperazin-1-yl]propyl]-3,4-dimethyl-[1,2]oxazolo[3,4-d]pyridazin-7-one
• CAS: 502135-06-0
• 化学式: C₂₀H₂₄ClN₅O₂
• 分子量: 401.896
• InChiKey: RZNMYLDSBOBPCJ-UHFFFAOYSA-N

物化性质

• 沸点：
  604.2±65.0 °C(Predicted)
• 密度：
  1.36±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  28
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  65.2
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  6-{3-[4-(3-Chloro-phenyl)-piperazin-1-yl]-propyl}-3,4-dimethyl-6H-isoxazolo[3,4-d]pyridazin-7-one 在 sodium tetrahydroborate 、 ammonium formate 作用下， 以 甲醇 、 乙醇 为溶剂， 反应 2.0h， 生成 4-amino-2-{3-[4-(3-chlorophenyl)piperazin-1-yl]propyl}-5-(1-hydroxyethyl)-6-methylpyridazin-3(2H)-one
  参考文献：
  名称：

  [(3-Chlorophenyl)piperazinylpropyl]pyridazinones and Analogues as Potent Antinociceptive Agents

  摘要：

  A number of [(3-chlorophenyl)piperazinylpropyl]pyridazinones and the corresponding isoxazolo-pyridazinones, showing the arylpiperazinyl substructure present in very potent antinociceptive agents reported in the literature, were synthesized and tested for their analgesic activity. The investigated compounds showed antinociceptive properties in the mouse hot-plate test (thermal nociceptive stimulus) after systemic administration with an efficacy similar to that exerted by morphine. The increase of the pain threshold induced by the compounds labeled 5a, 7, 8, and 11 was prevented by reserpine, suggesting the involvement of the noradrenergic and/or serotoninergic system in their mechanism of action. Among them, 7 and 11 showed the highest analgesic potency and efficacy together with a good ratio (133 and 200, respectively) of the minimal nontoxic dose (MNTD) to the minimal analgesic dose (MAD). Furthermore, they were also active after icv administration and in the presence of a chemical, painful stimulus (abdominal constriction test).

  DOI：

  10.1021/jm021057u
• 作为产物：
  描述：

  1-(3-氯苯基)哌嗪 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 6-{3-[4-(3-Chloro-phenyl)-piperazin-1-yl]-propyl}-3,4-dimethyl-6H-isoxazolo[3,4-d]pyridazin-7-one
  参考文献：
  名称：

  [(3-Chlorophenyl)piperazinylpropyl]pyridazinones and Analogues as Potent Antinociceptive Agents

  摘要：

  A number of [(3-chlorophenyl)piperazinylpropyl]pyridazinones and the corresponding isoxazolo-pyridazinones, showing the arylpiperazinyl substructure present in very potent antinociceptive agents reported in the literature, were synthesized and tested for their analgesic activity. The investigated compounds showed antinociceptive properties in the mouse hot-plate test (thermal nociceptive stimulus) after systemic administration with an efficacy similar to that exerted by morphine. The increase of the pain threshold induced by the compounds labeled 5a, 7, 8, and 11 was prevented by reserpine, suggesting the involvement of the noradrenergic and/or serotoninergic system in their mechanism of action. Among them, 7 and 11 showed the highest analgesic potency and efficacy together with a good ratio (133 and 200, respectively) of the minimal nontoxic dose (MNTD) to the minimal analgesic dose (MAD). Furthermore, they were also active after icv administration and in the presence of a chemical, painful stimulus (abdominal constriction test).

  DOI：

  10.1021/jm021057u

文献信息

• [(3-Chlorophenyl)piperazinylpropyl]pyridazinones and Analogues as Potent Antinociceptive Agents
  作者：Maria Paola Giovannoni、Claudia Vergelli、Carla Ghelardini、Nicoletta Galeotti、Alessandro Bartolini、Vittorio Dal Piaz

  DOI：10.1021/jm021057u

  日期：2003.3.1

  A number of [(3-chlorophenyl)piperazinylpropyl]pyridazinones and the corresponding isoxazolo-pyridazinones, showing the arylpiperazinyl substructure present in very potent antinociceptive agents reported in the literature, were synthesized and tested for their analgesic activity. The investigated compounds showed antinociceptive properties in the mouse hot-plate test (thermal nociceptive stimulus) after systemic administration with an efficacy similar to that exerted by morphine. The increase of the pain threshold induced by the compounds labeled 5a, 7, 8, and 11 was prevented by reserpine, suggesting the involvement of the noradrenergic and/or serotoninergic system in their mechanism of action. Among them, 7 and 11 showed the highest analgesic potency and efficacy together with a good ratio (133 and 200, respectively) of the minimal nontoxic dose (MNTD) to the minimal analgesic dose (MAD). Furthermore, they were also active after icv administration and in the presence of a chemical, painful stimulus (abdominal constriction test).