3-(4-甲基哌嗪-1-基)-1H-吲哚 | 859164-44-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪烷类
• 中文名称: 3-(4-甲基哌嗪-1-基)-1H-吲哚
• 英文名称: 3-(4-methyl-piperazin-1-yl)-1H-indole
• 英文别名: 3-(4-Methylpiperazin-1-YL)-1H-indole
• CAS: 859164-44-6
• 化学式: C₁₃H₁₇N₃
• 分子量: 215.298
• InChiKey: DZCWFZGVUTXGDD-UHFFFAOYSA-N

物化性质

• 熔点：
  194 °C
• 沸点：
  391.8±32.0 °C(Predicted)
• 密度：
  1.162±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  22.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-(4-甲基哌嗪-1-基)-1H-吲哚 、 2-溴苯磺酰氯 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 、 mineral oil 为溶剂， 反应 2.75h， 生成 1-(2-bromophenylsulfonyl)-3-(4-methylpiperazin-1-yl)-1H-indole
  参考文献：
  名称：

  Indole-3-piperazinyl derivatives: Novel chemical class of 5-HT6 receptor antagonists

  摘要：

  N-1-Arylsulfonyl-3-piperazinyl indole derivatives were designed and identified as a novel class of 5-HT6 receptors ligands. All the compounds have high affinity and antagonist activity towards 5-HT6 receptor. The compound 7a (K-i = 3.4 nM, functional assay IC50 = 310 nM) shows enhanced cognitive effect when tested in NORT and Morris water maze models. Synthesis, SAR and PK profile of these novel compounds constitute the subject matter of this Letter. (C) 2010 Published by Elsevier Ltd.

  DOI：

  10.1016/j.bmcl.2010.11.001
• 作为产物：
  描述：

  1-(3-(4-methylpiperazin-1-yl)-1H-indol-1-yl)ethan-1-one 在 potassium hydroxide 作用下， 以 乙醇 为溶剂， 生成 3-(4-甲基哌嗪-1-基)-1H-吲哚
  参考文献：
  名称：

  Indole-3-piperazinyl derivatives: Novel chemical class of 5-HT6 receptor antagonists

  摘要：

  N-1-Arylsulfonyl-3-piperazinyl indole derivatives were designed and identified as a novel class of 5-HT6 receptors ligands. All the compounds have high affinity and antagonist activity towards 5-HT6 receptor. The compound 7a (K-i = 3.4 nM, functional assay IC50 = 310 nM) shows enhanced cognitive effect when tested in NORT and Morris water maze models. Synthesis, SAR and PK profile of these novel compounds constitute the subject matter of this Letter. (C) 2010 Published by Elsevier Ltd.

  DOI：

  10.1016/j.bmcl.2010.11.001

文献信息

• Cb1 antagonist compounds
  申请人：Allen Rebecca Jennifer

  公开号：US20070088018A1

  公开（公告）日：2007-04-19

  Novel compounds of structural formula (I) are disclosed. As modulators of the Cannabinoid-1 (CB1) receptor, these compounds are useful in the treatment, prevention and suppression of diseases mediated by the CB1 receptor. As such, compounds of the present invention are useful as in the treatment, prevention and suppression of psychosis, memory deficits, cognitive disorders, migraine, neuropathy, neuro-inflammatory disorders (e.g., multiple sclerosis, Guillain-Barre syndrome and the inflammatory sequelae of viral encephalitis), cerebral vascular accidents, head trauma, anxiety disorders, stress, epilepsy, Parkinson's disease, and schizophrenia. The compounds are also useful for the treatment of substance abuse disorders, particularly to opiates, alcohol, and nicotine. The compounds are also useful for the treatment of obesity or eating disorders associated with excessive food intake and complications associated therewith.

  本发明揭示了化学结构式（I）的新型化合物。作为大麻素-1（CB1）受体的调节剂，这些化合物在治疗、预防和抑制由CB1受体介导的疾病方面具有用途。因此，本发明的化合物在治疗、预防和抑制精神病、记忆障碍、认知障碍、偏头痛、神经病、神经炎症性疾病（例如多发性硬化症、吉兰-巴雷综合征和病毒性脑炎的炎症后遗症）、脑血管意外、头部创伤、焦虑症、压力、癫痫、帕金森病和精神分裂症方面具有用途。这些化合物还可用于治疗物质滥用障碍，特别是阿片类药物、酒精和尼古丁。这些化合物还可用于治疗与过度食物摄入及其并发症相关的肥胖症或进食障碍。
• CB1 antagonist compounds
  申请人：Eli Lilly and Company

  公开号：US07276516B2

  公开（公告）日：2007-10-02

  Novel compounds of structural formula (I) are disclosed. As modulators of the Cannabinoid-1 (CB1) receptor, these compounds are useful in the treatment, prevention and suppression of diseases mediated by the CB1 receptor. As such, compounds of the present invention are useful as in the treatment, prevention and suppression of psychosis, memory deficits, cognitive disorders, migraine, neuropathy, neuro-inflammatory disorders (e.g., multiple sclerosis, Guillain-Barre syndrome and the inflammatory sequelae of viral encephalitis), cerebral vascular accidents, head trauma, anxiety disorders, stress, epilepsy, Parkinson's disease, and schizophrenia. The compounds are also useful for the treatment of substance abuse disorders, particularly to opiates, alcohol, and nicotine. The compounds are also useful for the treatment of obesity or eating disorders associated with excessive food intake and complications associated therewith

  揭示了结构式(I)的新型化合物。作为Cannabinoid-1（CB1）受体的调节剂，这些化合物在治疗、预防和抑制由CB1受体介导的疾病方面非常有用。因此，本发明的化合物在治疗、预防和抑制精神病、记忆障碍、认知障碍、偏头痛、神经病、神经炎症性疾病（例如多发性硬化症、格林-巴利综合征和病毒性脑炎的炎症后遗症）、脑血管意外、头部创伤、焦虑症、压力、癫痫、帕金森病和精神分裂症方面非常有用。这些化合物也可用于治疗物质滥用障碍，特别是阿片类、酒精和尼古丁。这些化合物也可用于治疗与过度进食和相关并发症相关的肥胖或进食障碍。
• CB1 MODULATOR COMPOUNDS
  申请人：Allen Jennifer Rebecca

  公开号：US20080287504A1

  公开（公告）日：2008-11-20

  Novel compounds of structural formula (I) are disclosed. As modulators of the Cannabinoid-1 (CB1) receptor, these compounds are useful in the treatment, prevention and suppression of diseases mediated by the CB1 receptor. As such, compounds of the present invention are useful as in the treatment, prevention and suppression of psychosis, memory deficits, cognitive disorders, migraine, neuropathy, neuro-inflammatory disorders (e.g., multiple sclerosis, Guillain-Barre syndrome and the inflammatory sequelae of viral encephalitis), cerebral vascular accidents, head trauma, anxiety disorders, stress, epilepsy, Parkinson's disease, and schizophrenia. The compounds are also useful for the treatment of substance abuse disorders, particularly to opiates, alcohol, and nicotine. The compounds are also useful for the treatment of obesity or eating disorders associated with excessive food intake and complications associated therewith.

  本发明揭示了化学式 (I) 的新型化合物。作为大麻素-1（CB1）受体的调节剂，这些化合物在治疗、预防和抑制由CB1受体介导的疾病方面具有用途。因此，本发明的化合物在治疗、预防和抑制精神病、记忆障碍、认知障碍、偏头痛、神经病、神经炎症性疾病（例如多发性硬化症、格林-巴利综合症和病毒性脑炎的炎症后遗症）、脑血管意外、头部创伤、焦虑症、压力、癫痫、帕金森病和精神分裂症方面具有用途。这些化合物还对治疗物质滥用障碍特别是对阿片类、酒精和尼古丁的治疗具有用途。这些化合物还对治疗与过度食物摄入和相关并发症有关的肥胖症或进食障碍具有用途。
• CB1 modulator compounds
  申请人：Eli Lilly and Company

  公开号：US07595339B2

  公开（公告）日：2009-09-29

  Novel compounds of structural formula (I) are disclosed. As modulators of the Cannabinoid-1 (CB1) receptor, these compounds are useful in the treatment, prevention and suppression of diseases mediated by the CB1 receptor. As such, compounds of the present invention are useful as in the treatment, prevention and suppression of psychosis, memory deficits, cognitive disorders, migraine, neuropathy, neuro-inflammatory disorders (e.g., multiple sclerosis, Guillain-Barre syndrome and the inflammatory sequelae of viral encephalitis), cerebral vascular accidents, head trauma, anxiety disorders, stress, epilepsy, Parkinson's disease, and schizophrenia. The compounds are also useful for the treatment of substance abuse disorders, particularly to opiates, alcohol, and nicotine. The compounds are also useful for the treatment of obesity or eating disorders associated with excessive food intake and complications associated therewith.

  本发明揭示了结构式（I）的新化合物。作为Cannabinoid-1（CB1）受体的调节剂，这些化合物在治疗、预防和抑制由CB1受体介导的疾病方面非常有用。因此，本发明的化合物在治疗、预防和抑制精神病、记忆障碍、认知障碍、偏头痛、神经病变、神经炎性疾病（例如多发性硬化症、格林-巴利综合征和病毒性脑炎的炎症后遗症）、脑血管意外、头部创伤、焦虑症、压力、癫痫、帕金森病和精神分裂症方面非常有用。这些化合物还可用于治疗物质滥用障碍，特别是阿片类药物、酒精和尼古丁。这些化合物还可用于治疗与过度进食和相关并发症相关的肥胖症或进食障碍。
• US7276516B2
  申请人：——

  公开号：US7276516B2

  公开（公告）日：2007-10-02