2-[(hexahydro-2,5-methanopentalene-3a-carbonyl)-amino]-4,5,6,7-tetrahydrothieno[2,3-c]pyridine-3-carboxylic acid propylamide | 1101856-87-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 噻吩并吡啶类
• 英文名称: 2-[(hexahydro-2,5-methanopentalene-3a-carbonyl)-amino]-4,5,6,7-tetrahydrothieno[2,3-c]pyridine-3-carboxylic acid propylamide
• 英文别名: N-propyl-2-(tricyclo[3.3.1.03,7]nonane-3-carbonylamino)-4,5,6,7-tetrahydrothieno[2,3-c]pyridine-3-carboxamide
• CAS: 1101856-87-4
• 化学式: C₂₁H₂₉N₃O₂S
• 分子量: 387.546
• InChiKey: BWGIYWVDKHISHC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  27
• 可旋转键数：
  5
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  98.5
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  4-哌啶酮 在 吗啉 、 水 、 1-羟基苯并三唑 、 sulfur 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 、 potassium hydroxide 作用下， 以 四氢呋喃 、 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 31.0h， 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

文献信息

• NOVEL COMPOUNDS AS CANNABINOID RECEPTOR LIGANDS
  申请人：Carroll William A.

  公开号：US20090018114A1

  公开（公告）日：2009-01-15

  The present application relates to cannabinoid receptor ligands containing compounds of formula (I) wherein A, R 1 , R 2 , and R 3 are as defined in the specification. The present application also relates to compositions comprising such compounds, and methods of treating conditions and disorders using such compounds and compositions.

  本申请涉及含有式(I)化合物的大麻素受体配体，其中A、R1、R2和R3如规范中所定义。本申请还涉及包含这种化合物的组合物，以及使用这种化合物和组合物治疗疾病和疾病的方法。
• US8338623B2
  申请人：——

  公开号：US8338623B2

  公开（公告）日：2012-12-25
• Synthesis and evaluation of 2-amido-3-carboxamide thiophene CB2 receptor agonists for pain management
  作者：Derek W. Nelson、Jennifer M. Frost、Karin R. Tietje、Alan S. Florjancic、Keith Ryther、William A. Carroll、Michael J. Dart、Anthony V. Daza、Bradley A. Hooker、George K. Grayson、Yihong Fan、Tiffany R. Garrison、Odile F. El-Kouhen、Betty Yao、Madhavi Pai、Prasant Chandran、Chang Zhu、Gin C. Hsieh、Michael D. Meyer

  DOI：10.1016/j.bmcl.2012.01.121

  日期：2012.4

  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.