(R)-5-(4-(2-((tert-butyldimethylsilyl)oxy)ethyl)-2-methylpiperazin-1-yl)-6-chloro-1,3-dihydro-2H-benzo[d]imidazole-2-thione | 1042106-74-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪烷类
• 英文名称: (R)-5-(4-(2-((tert-butyldimethylsilyl)oxy)ethyl)-2-methylpiperazin-1-yl)-6-chloro-1,3-dihydro-2H-benzo[d]imidazole-2-thione
• CAS: 1042106-74-0
• 化学式: C₂₀H₃₃ClN₄OSSi
• 分子量: 441.113
• InChiKey: UNELDELDZGURTQ-CQSZACIVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.41
• 重原子数：
  28.0
• 可旋转键数：
  5.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  47.29
• 氢给体数：
  2.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (R)-5-(4-(2-((tert-butyldimethylsilyl)oxy)ethyl)-2-methylpiperazin-1-yl)-6-chloro-1,3-dihydro-2H-benzo[d]imidazole-2-thione 、 叔丁醇 在 三氟乙酸 作用下， 反应 16.0h， 以78%的产率得到2-(tert-butylthio)-5-chloro-6-[(2R)-4-(2-hydroxyethyl)-2-methylpiperazin-1-yl]-1H-benzimidazole
  参考文献：
  名称：

  Novel ORL1-selective antagonists with oral bioavailability and brain penetrability

  摘要：

  Following the discovery of 5-chloro-6-[piperazin-1-yl]-1H-benzimidazole as a novel pharmacophore for potent and selective ORL1 antagonist activity, optimization of this new lead by introduction of a methyl substitution on the piperazine ring resulted in a highly potent and selective, orally available, and brain penetrable ORL1 antagonist, 2-(tert-butylthio)-5-chloro-6-[(2R)-4-(2-hydroxyethyl)-2-methylpiperazin-1-yl]-1 H-benzimidazole. Stereochemistry of the methyl substituent on the piperazine ring to control the functional activity of other opioid receptors is also described. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2008.04.037
• 作为产物：
  描述：

  二硫化碳 、 在 sodium hydroxide 作用下， 以 甲醇 、 水 为溶剂， 反应 2.0h， 以100%的产率得到(R)-5-(4-(2-((tert-butyldimethylsilyl)oxy)ethyl)-2-methylpiperazin-1-yl)-6-chloro-1,3-dihydro-2H-benzo[d]imidazole-2-thione
  参考文献：
  名称：

  Novel ORL1-selective antagonists with oral bioavailability and brain penetrability

  摘要：

  Following the discovery of 5-chloro-6-[piperazin-1-yl]-1H-benzimidazole as a novel pharmacophore for potent and selective ORL1 antagonist activity, optimization of this new lead by introduction of a methyl substitution on the piperazine ring resulted in a highly potent and selective, orally available, and brain penetrable ORL1 antagonist, 2-(tert-butylthio)-5-chloro-6-[(2R)-4-(2-hydroxyethyl)-2-methylpiperazin-1-yl]-1 H-benzimidazole. Stereochemistry of the methyl substituent on the piperazine ring to control the functional activity of other opioid receptors is also described. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2008.04.037