N-(2-(1H-indol-3-yl)ethyl)-1-(4-(trifluoromethyl)phenyl)methanimine | 289498-46-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: N-(2-(1H-indol-3-yl)ethyl)-1-(4-(trifluoromethyl)phenyl)methanimine
• CAS: 289498-46-0
• 化学式: C₁₈H₁₅F₃N₂
• 分子量: 316.326
• InChiKey: TXJTZLXZBOBAEP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.85
• 重原子数：
  23.0
• 可旋转键数：
  4.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  28.15
• 氢给体数：
  1.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  N-(2-(1H-indol-3-yl)ethyl)-1-(4-(trifluoromethyl)phenyl)methanimine 、 ethyl 4-hydroxy-4-(4-methoxyphenyl)-2-oxobut-3-enoate 以 乙醇 为溶剂， 反应 24.0h， 以12 mg的产率得到3-hydroxy-1-(2-(indol-3-yl)ethyl)-4-(4-methoxybenzoyl)-5-(4-trifluoromethylphenyl)-1,5-dihydro-2H-pyrrol-2-one
  参考文献：
  名称：

  Identification of Trypanosoma brucei leucyl-tRNA synthetase inhibitors by pharmacophore- and docking-based virtual screening and synthesis

  摘要：

  Human African trypanosomiasis (HAT), caused by the protozoan parasite Trypanosoma brucei, is a neglected fatal disease. Leucyl-tRNA synthetase (LeuRS), which has been successfully applied in the development of antifungal agent, represents a potential antiprotozoal drug target. In this study, a 3D model of T. brucei LeuRS (TbLeuRS) synthetic active site was constructed and subjected to virtual screening using a combination of pharmacophore- and docking-based methods. A new 2-pyrrolinone scaffold was discovered and the structure-activity relationship (SAR) studies aided by the docking model and organic synthesis were carried out. Compounds with various substituents on R-1, R-2 and R-3 were synthesized and their SAR was discussed. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.12.035
• 作为产物：
  描述：

  对三氟甲基苯甲醛 、 色胺 以 乙醇 为溶剂， 反应 1.0h， 生成 N-(2-(1H-indol-3-yl)ethyl)-1-(4-(trifluoromethyl)phenyl)methanimine
  参考文献：
  名称：

  Identification of Trypanosoma brucei leucyl-tRNA synthetase inhibitors by pharmacophore- and docking-based virtual screening and synthesis

  摘要：

  Human African trypanosomiasis (HAT), caused by the protozoan parasite Trypanosoma brucei, is a neglected fatal disease. Leucyl-tRNA synthetase (LeuRS), which has been successfully applied in the development of antifungal agent, represents a potential antiprotozoal drug target. In this study, a 3D model of T. brucei LeuRS (TbLeuRS) synthetic active site was constructed and subjected to virtual screening using a combination of pharmacophore- and docking-based methods. A new 2-pyrrolinone scaffold was discovered and the structure-activity relationship (SAR) studies aided by the docking model and organic synthesis were carried out. Compounds with various substituents on R-1, R-2 and R-3 were synthesized and their SAR was discussed. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.12.035