5-(piperazin-1-yl)-2-(trifluoromethyl)-1H-benzo[d]imidazole | 1046790-72-0

• 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: 5-(piperazin-1-yl)-2-(trifluoromethyl)-1H-benzo[d]imidazole
• 英文别名: 6-piperazin-1-yl-2-(trifluoromethyl)-1H-benzimidazole
• CAS: 1046790-72-0
• 化学式: C₁₂H₁₃F₃N₄
• 分子量: 270.257
• InChiKey: VCPKTQMILYKDGH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  19
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  44
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2-(3-azido-2-nitrophenoxy)acetaldehyde 、 5-(piperazin-1-yl)-2-(trifluoromethyl)-1H-benzo[d]imidazole 在 三乙酰氧基硼氢化钠 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 生成 5-{4-[2-(3-azido-2-nitrophenoxy)ethyl]piperazin-1-yl}-2-(trifluoromethyl)-1H-benzo[d]imidazole
  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：

  2-氨基-5-(4-Boc-1-哌嗪)苯胺 、 三氟乙酸 反应 2.0h， 生成 5-(piperazin-1-yl)-2-(trifluoromethyl)-1H-benzo[d]imidazole
  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

文献信息

• [EN] NOVEL 5-HYDROXYTRYPTAMINE RECEPTOR 7 ACTIVITY MODULATORS AND THEIR METHOD OF USE<br/>[FR] NOUVEAUX MODULATEURS DE L'ACTIVITÉ DU RÉCEPTEUR DE 5-HYDROXYTRYPTAMINE 7 ET LEUR PROCÉDÉ D'UTILISATION
  申请人：UNIV TEMPLE

  公开号：WO2016040554A1

  公开（公告）日：2016-03-17

  Pharmaceutical compositions of the invention comprise functionalized lactone derivatives having a disease-modifying action in the treatment of diseases associated with dysregulation of 5-hydroxytryptamine receptor 7 activity.

  本发明的药物组合物包括具有疾病修饰作用的功能化内酯衍生物，在治疗与5-羟色胺受体7活性失调相关的疾病方面发挥作用。
• 5-hydroxytryptamine receptor 7 activity modulators and their method of use
  申请人：Temple University—Of the Commonwealth System of Higher Education

  公开号：US10544117B2

  公开（公告）日：2020-01-28

  Pharmaceutical compositions of the invention comprise functionalized lactone derivatives of formula (I) having a disease-modifying action in the treatment of diseases associated with dysregulation of 5-hydroxytryptamine receptor 7 activity.

  本发明的药物组合物包括式 (I) 的官能化内酯衍生物 在治疗与 5-羟色胺受体 7 活性失调有关的疾病时具有调节疾病的作用。
• EP3200589A1
  申请人：——

  公开号：EP3200589A1

  公开（公告）日：2017-08-09
• Novel 5-Hydroxytryptamine Receptor 7 Activity Modulators and Their Method of Use
  申请人：Temple University-Of the Commonwealth system of Higher Education

  公开号：US20170298037A1

  公开（公告）日：2017-10-19

  Pharmaceutical compositions of the invention comprise functionalized lactone derivatives having a disease-modifying action in the treatment of diseases associated with dysregulation of 5-hydroxytryptamine receptor 7 activity.
• NOVEL 5-HYDROXYTRYPTAMINE RECEPTOR 7 ACTIVITY MODULATORS AND THEIR METHOD OF USE
  申请人：Temple University-Of The Commonwealth System of Higher Education

  公开号：US20200223810A1

  公开（公告）日：2020-07-16

  Pharmaceutical compositions of the invention comprise functionalized lactone derivatives having a disease-modifying action in the treatment of diseases associated with dysregulation of 5-hydroxytryptamine receptor 7 activity.