2-Tert-butyl-5-[(4-methoxyphenyl)methylsulfanyl]-1-(thian-4-ylmethyl)benzimidazole | 1010114-34-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并咪唑类
• 英文名称: 2-Tert-butyl-5-[(4-methoxyphenyl)methylsulfanyl]-1-(thian-4-ylmethyl)benzimidazole
• CAS: 1010114-34-7
• 化学式: C₂₅H₃₂N₂OS₂
• 分子量: 440.674
• InChiKey: YRCIBMNYWLNXFT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.5
• 重原子数：
  30
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  77.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-Tert-butyl-5-[(4-methoxyphenyl)methylsulfanyl]-1-(thian-4-ylmethyl)benzimidazole 在 caesium carbonate 、 间氯过氧苯甲酸 、 三氟乙酸 作用下， 以 氯仿 、 丙酮 为溶剂， 生成 4-[(2-Tert-butyl-5-ethylsulfonylbenzimidazol-1-yl)methyl]thiane 1,1-dioxide
  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-硝基-5-氯苯胺 在 吡啶 、 铁粉 、 sodium cyanoborohydride 、 溶剂黄146 、 potassium hydroxide 作用下， 以 乙醇 、 二氯甲烷 、 水 为溶剂， 反应 6.0h， 生成 2-Tert-butyl-5-[(4-methoxyphenyl)methylsulfanyl]-1-(thian-4-ylmethyl)benzimidazole
  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

• WO2008/119694
  申请人：——

  公开号：——

  公开（公告）日：——
• BENZIMIDAZOLE CANNABINOID AGONISTS
  申请人：Janssen Pharmaceutica N.V.

  公开号：EP2142531B1

  公开（公告）日：2015-07-08
• BENZIMIDAZOLE CANNABINOID AGONISTS BEARING A SUBSTITUTED HETEROCYCLIC GROUP
  申请人：Gijsen Henricus Jacobus Maria

  公开号：US20090312339A1

  公开（公告）日：2009-12-17

  The present invention is related to novel benzimidazole compounds of formula (I) having cannabinoid receptor agonistic properties, pharmaceutical compositions comprising these compounds, chemical processes for preparing these compounds and their use in the treatment of diseases linked to the mediation of the cannabinoid receptors in animals, in particular humans.
• US8193369B2
  申请人：——

  公开号：US8193369B2

  公开（公告）日：2012-06-05
• US8524757B2
  申请人：——

  公开号：US8524757B2

  公开（公告）日：2013-09-03