2-(3-azido-2-nitrophenoxy)-1-{4-[2-(trifluoromethyl)-1H-benzo[d]imidazol-4-yl]piperazin-1-yl}ethanone | 1046790-65-1

• 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: 2-(3-azido-2-nitrophenoxy)-1-{4-[2-(trifluoromethyl)-1H-benzo[d]imidazol-4-yl]piperazin-1-yl}ethanone
• CAS: 1046790-65-1
• 化学式: C₂₀H₁₇F₃N₈O₄
• 分子量: 490.401
• InChiKey: PTXROEKRLDLELF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.16
• 重原子数：
  35.0
• 可旋转键数：
  6.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  153.36
• 氢给体数：
  1.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  2-(3-azido-2-nitrophenoxy)-1-{4-[2-(trifluoromethyl)-1H-benzo[d]imidazol-4-yl]piperazin-1-yl}ethanone 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 为溶剂， 反应 5.0h， 生成
  参考文献：
  名称：

  2-Phenyl-4-piperazinylbenzimidazoles: Orally active inhibitors of the gonadotropin releasing hormone (GnRH) receptor

  摘要：

  Antagonism of the gonadotropin releasing hormone (GnRH) receptor has shown positive clinical results in numerous reproductive tissue disorders such as endometriosis, prostate cancer and others. Traditional therapy has been limited to peptide agonists and antagonists. Recently, small molecule GnRH antagonists have emerged as potentially new treatments. This article describes the discovery of 2-phenyl-4-piperazinylbenzimidazoles as small molecule GnRH antagonists with nanomolar potency in in vitro binding and functional assays, excellent bioavailability (rat % F > 70) and demonstrated oral activity in a rat model having shown significant serum leuteinizing hormone (LH) suppression. (c) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2008.05.024
• 作为产物：
  描述：

  4-(piperazin-1-yl)-2-(trifluoromethyl)-1H-benzo[d]imidazole 、 2-(3-azido-2-nitrophenoxy)acetic acid 在 N,N-二异丙基乙胺 、 N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 以88 mg的产率得到2-(3-azido-2-nitrophenoxy)-1-{4-[2-(trifluoromethyl)-1H-benzo[d]imidazol-4-yl]piperazin-1-yl}ethanone
  参考文献：
  名称：

  2-Phenyl-4-piperazinylbenzimidazoles: Orally active inhibitors of the gonadotropin releasing hormone (GnRH) receptor

  摘要：

  Antagonism of the gonadotropin releasing hormone (GnRH) receptor has shown positive clinical results in numerous reproductive tissue disorders such as endometriosis, prostate cancer and others. Traditional therapy has been limited to peptide agonists and antagonists. Recently, small molecule GnRH antagonists have emerged as potentially new treatments. This article describes the discovery of 2-phenyl-4-piperazinylbenzimidazoles as small molecule GnRH antagonists with nanomolar potency in in vitro binding and functional assays, excellent bioavailability (rat % F > 70) and demonstrated oral activity in a rat model having shown significant serum leuteinizing hormone (LH) suppression. (c) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2008.05.024