tert-butyl 4-{2-nitro-3-[(trifluoroacetyl)amino]phenyl}piperazine-1-carboxylate | 1046790-77-5

• 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: tert-butyl 4-{2-nitro-3-[(trifluoroacetyl)amino]phenyl}piperazine-1-carboxylate
• CAS: 1046790-77-5
• 化学式: C₁₇H₂₁F₃N₄O₅
• 分子量: 418.373
• InChiKey: MHPAXSVRHPRVPN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.15
• 重原子数：
  29.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  105.02
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  甲醇 、 tert-butyl 4-{2-nitro-3-[(trifluoroacetyl)amino]phenyl}piperazine-1-carboxylate 在 偶氮二甲酸二异丙酯 、 三苯基膦 作用下， 以 四氢呋喃 为溶剂， 反应 15.0h， 以89%的产率得到tert-butyl 4-{3-[methyl(trifluoroacetyl)amino]-2-nitrophenyl}piperazine-1-carboxylate
  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-(3-氨基-2-硝基苯基)哌嗪-1-羧酸叔丁酯 、 三氟乙酸酐 在 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以99%的产率得到tert-butyl 4-{2-nitro-3-[(trifluoroacetyl)amino]phenyl}piperazine-1-carboxylate
  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