2-(octahydro-2,5-methanopentalene-3a-carboxamido)-4,5,6,7-tetrahydrothieno[2,3-c]pyridine-3-carboxylic acid | 1370345-51-9

• 分子结构分类: 有机化合物 - 有机杂环化合物
• 英文名称: 2-(octahydro-2,5-methanopentalene-3a-carboxamido)-4,5,6,7-tetrahydrothieno[2,3-c]pyridine-3-carboxylic acid
• CAS: 1370345-51-9
• 化学式: C₁₈H₂₂N₂O₃S
• 分子量: 346.45
• InChiKey: MLDFJDFTVJBPHH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.86
• 重原子数：
  24.0
• 可旋转键数：
  3.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  78.43
• 氢给体数：
  3.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  正丙胺 、 2-(octahydro-2,5-methanopentalene-3a-carboxamido)-4,5,6,7-tetrahydrothieno[2,3-c]pyridine-3-carboxylic acid 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 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 生成 2-[(hexahydro-2,5-methanopentalene-3a-carbonyl)-amino]-4,5,6,7-tetrahydrothieno[2,3-c]pyridine-3-carboxylic acid propylamide
  参考文献：
  名称：

  Synthesis and evaluation of 2-amido-3-carboxamide thiophene CB2 receptor agonists for pain management

  摘要：

  SAR studies on a series of thiophene amide derivatives provided CB2 receptor agonists. The activity of the compounds was characterized by radioligand binding determination, multiple functional assays, ADME, and pharmacokinetic studies. A representative compound with selectivity for CB2 over CB1 effectively produced analgesia in behavioral models of neuropathic, inflammatory, and postsurgical pain. Control experiments using a CB2 antagonist demonstrated the efficacy in the pain models resulted from CB2 agonism. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.01.121
• 作为产物：
  描述：

  4-哌啶酮 在 吗啉 、 水 、 sulfur 、 三乙胺 、 potassium hydroxide 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 反应 7.0h， 生成 2-(octahydro-2,5-methanopentalene-3a-carboxamido)-4,5,6,7-tetrahydrothieno[2,3-c]pyridine-3-carboxylic acid
  参考文献：
  名称：

  Synthesis and evaluation of 2-amido-3-carboxamide thiophene CB2 receptor agonists for pain management

  摘要：

  SAR studies on a series of thiophene amide derivatives provided CB2 receptor agonists. The activity of the compounds was characterized by radioligand binding determination, multiple functional assays, ADME, and pharmacokinetic studies. A representative compound with selectivity for CB2 over CB1 effectively produced analgesia in behavioral models of neuropathic, inflammatory, and postsurgical pain. Control experiments using a CB2 antagonist demonstrated the efficacy in the pain models resulted from CB2 agonism. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.01.121