2-(1,3-benzodioxol-5-yl)-N-[1-(1H-1,2,3-benzotriazol-1-yl)-2,2-dimethylpropyl]acetamide | 861393-68-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并三唑类
• 英文名称: 2-(1,3-benzodioxol-5-yl)-N-[1-(1H-1,2,3-benzotriazol-1-yl)-2,2-dimethylpropyl]acetamide
• 英文别名: 2-(1,3-benzodioxol-5-yl)-N-[1-(benzotriazol-1-yl)-2,2-dimethylpropyl]acetamide
• CAS: 861393-68-2
• 化学式: C₂₀H₂₂N₄O₃
• 分子量: 366.42
• InChiKey: MJWDYIPMWPBJTR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  27
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  78.3
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-(1,3-benzodioxol-5-yl)-N-[1-(1H-1,2,3-benzotriazol-1-yl)-2,2-dimethylpropyl]acetamide 、 N''-cyano-N-(2-methylphenyl)guanidine 在 caesium carbonate 作用下， 以 乙腈 为溶剂， 反应 10.0h， 生成 2-(1,3-benzodioxol-5-yl)-N-[1-({(cyanoimino)[(2-methylphenyl)amino]methyl}amino)-2,2-dimethylpropyl]acetamide
  参考文献：
  名称：

  Discovery and Biological Evaluation of Novel Cyanoguanidine P2X₇ Antagonists with Analgesic Activity in a Rat Model of Neuropathic Pain

  摘要：

  We disclose the design of a novel series of cyanoguanidines that are potent (IC50 similar or equal to 10-100 nM) and selective (>= 100-fold) P2X(7) receptor antagonists against the other P2 receptor subtypes such as the P2Y(2), P2X(4), and P2X(3). We also found that these P2X(7) antagonists effectively reduced nociception in a rat model of neuropathic pain (Chung model). Particularly, analogue 53 proved to be effective in the Chung model, with an ED50 of 38 mu mol/kg after intraperitoneal administration. In addition compound 53 exhibited antiallodynic effects following oral administration and maintained its efficacy following repeated administration in the Chung model. These results suggest an important role of P2X(7) receptors in neuropathic pain and therefore a potential use of P2X(7) antagonists as novel therapeutic tools for the treatment of this type of pain.

  DOI：

  10.1021/jm8015848
• 作为产物：
  描述：

  T406石油添加剂 、 胡椒乙酰胺 、 特戊醛 生成 2-(1,3-benzodioxol-5-yl)-N-[1-(1H-1,2,3-benzotriazol-1-yl)-2,2-dimethylpropyl]acetamide
  参考文献：
  名称：

  P2X7 antagonists for treating neuropathic pain

  摘要：

  本发明揭示了一种使用式I化合物或含有式I化合物的组合物治疗神经病性疼痛的方法。

  公开号：

  US20050171195A1

文献信息

• Cyanoamidine P2X7 antagonists for the treatment of pain
  申请人：Carroll A. William

  公开号：US20060025614A1

  公开（公告）日：2006-02-02

  Novel cyanoamidines compounds of formula (I) and (II) and their derivatives wherein R 1 -R 12 are as defined in the specification act as antagonists of the P2X 7 receptor. These compounds are particularly useful in the treatment of pain, inflammation and neurodegeneration states.

  新型氰胺基化合物的化学式(I)和(II)及其衍生物，其中R1-R12如规范中定义的作为P2X7受体的拮抗剂。这些化合物在治疗疼痛、炎症和神经退行性状态方面特别有用。
• P2X7 antagonists for treating neuropathic pain
  申请人：Carroll A. William

  公开号：US20050171195A1

  公开（公告）日：2005-08-04

  The present invention discloses a method for treating neuropathic pain using compounds of formula I or compositions containing compounds of formula I.

  本发明公开了一种利用式I化合物或含有式I化合物的组合物治疗神经病性疼痛的方法。
• Cyanoamidine P2X7 Antagonists for the Treatment of Pain
  申请人：Carroll A. William

  公开号：US20070232686A1

  公开（公告）日：2007-10-04

  Novel cyanoamidines compounds of formula (I) and (II) and their derivatives wherein R 1 -R 12 are as defined in the specification act as antagonists of the P2X 7 receptor. These compounds are particularly useful in the treatment of pain, inflammation and neurodegeneration states.

  化合物(I)和(II)以及它们的衍生物，其化学式中R1-R12如规范中定义，可作为P2X7受体的拮抗剂。这些化合物在治疗疼痛、炎症和神经退行性疾病方面特别有用。
• US7241776B2
  申请人：——

  公开号：US7241776B2

  公开（公告）日：2007-07-10
• Discovery and Biological Evaluation of Novel Cyanoguanidine P2X₇ Antagonists with Analgesic Activity in a Rat Model of Neuropathic Pain
  作者：Arturo Perez-Medrano、Diana L. Donnelly-Roberts、Prisca Honore、Gin C. Hsieh、Marian T. Namovic、Sridhar Peddi、Qi Shuai、Ying Wang、Connie R. Faltynek、Michael F. Jarvis、William A. Carroll

  DOI：10.1021/jm8015848

  日期：2009.5.28

  We disclose the design of a novel series of cyanoguanidines that are potent (IC50 similar or equal to 10-100 nM) and selective (>= 100-fold) P2X(7) receptor antagonists against the other P2 receptor subtypes such as the P2Y(2), P2X(4), and P2X(3). We also found that these P2X(7) antagonists effectively reduced nociception in a rat model of neuropathic pain (Chung model). Particularly, analogue 53 proved to be effective in the Chung model, with an ED50 of 38 mu mol/kg after intraperitoneal administration. In addition compound 53 exhibited antiallodynic effects following oral administration and maintained its efficacy following repeated administration in the Chung model. These results suggest an important role of P2X(7) receptors in neuropathic pain and therefore a potential use of P2X(7) antagonists as novel therapeutic tools for the treatment of this type of pain.