2-[5-(4-Chloropyridin-2-yl)pent-4-ynyl]isoindole-1,3-dione | 1355997-56-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异吲哚及其衍生物
• 英文名称: 2-[5-(4-Chloropyridin-2-yl)pent-4-ynyl]isoindole-1,3-dione
• 英文别名: 2-[5-(4-chloropyridin-2-yl)pent-4-ynyl]isoindole-1,3-dione
• CAS: 1355997-56-6
• 化学式: C₁₈H₁₃ClN₂O₂
• 分子量: 324.766
• InChiKey: RSDGBCIJSNQNIQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  50.3
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-[5-(4-Chloropyridin-2-yl)pent-4-ynyl]isoindole-1,3-dione 在 噻吩 、 tris-(dibenzylideneacetone)dipalladium(0) 、 platinum on carbon 、 氢气 、 caesium carbonate 、 三乙胺 、 间氯过氧苯甲酸 、 4,5-双二苯基膦-9,9-二甲基氧杂蒽 作用下， 以 1,4-二氧六环 、 甲醇 、 氯仿 为溶剂， 生成 2-(5-(4-((2-(tert-butyl)-1-((tetrahydro-2H-pyran-4-yl)methyl)-1H-benzo[d]imidazol-5-yl)sulfonyl)pyridin-2-yl)pentyl)isoindoline-1,3-dione
  参考文献：
  名称：

  5-Sulfonyl-benzimidazoles as selective CB2 agonists-Part 2

  摘要：

  In a previous communication, the SAR of a series of potent and selective 5-sulfonyl-benzimidazole CB2-receptor agonists was described. The lack of in vivo activity of compounds from this series was attributed to their poor solubility and metabolic stability. In this Letter, we report on the further optimization of this series, leading to the relatively polar and peripherically acting CB2 agonists 41 and 49. Although both compounds were not active in acute pain models, the less selective compound 41 displayed good, sustained activity in a chronic model of neuropathic pain without the tolerance observed with morphine. In addition, both 41 and 49 delayed the onset of clinical symptoms in an experimental model for Multiple sclerosis. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.10.091
• 作为产物：
  描述：

  2,4-二氯吡啶 、 N-(4-戊炔基)酞酰亚胺 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 三乙胺 作用下， 生成 2-[5-(4-Chloropyridin-2-yl)pent-4-ynyl]isoindole-1,3-dione
  参考文献：
  名称：

  5-Sulfonyl-benzimidazoles as selective CB2 agonists-Part 2

  摘要：

  In a previous communication, the SAR of a series of potent and selective 5-sulfonyl-benzimidazole CB2-receptor agonists was described. The lack of in vivo activity of compounds from this series was attributed to their poor solubility and metabolic stability. In this Letter, we report on the further optimization of this series, leading to the relatively polar and peripherically acting CB2 agonists 41 and 49. Although both compounds were not active in acute pain models, the less selective compound 41 displayed good, sustained activity in a chronic model of neuropathic pain without the tolerance observed with morphine. In addition, both 41 and 49 delayed the onset of clinical symptoms in an experimental model for Multiple sclerosis. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.10.091

文献信息

• 5-Sulfonyl-benzimidazoles as selective CB2 agonists-Part 2
  作者：Harrie J.M. Gijsen、Michel A.J. De Cleyn、Michel Surkyn、Guy R.E. Van Lommen、Bie M.P. Verbist、Marjoleen J.M.A. Nijsen、Theo Meert、Jean Van Wauwe、Jeroen Aerssens

  DOI：10.1016/j.bmcl.2011.10.091

  日期：2012.1

  In a previous communication, the SAR of a series of potent and selective 5-sulfonyl-benzimidazole CB2-receptor agonists was described. The lack of in vivo activity of compounds from this series was attributed to their poor solubility and metabolic stability. In this Letter, we report on the further optimization of this series, leading to the relatively polar and peripherically acting CB2 agonists 41 and 49. Although both compounds were not active in acute pain models, the less selective compound 41 displayed good, sustained activity in a chronic model of neuropathic pain without the tolerance observed with morphine. In addition, both 41 and 49 delayed the onset of clinical symptoms in an experimental model for Multiple sclerosis. (C) 2011 Elsevier Ltd. All rights reserved.