4-[4-(6-trifluoromethyl-1H-indol-2-yl)phenoxy]benzonitrile | 1162684-46-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: 4-[4-(6-trifluoromethyl-1H-indol-2-yl)phenoxy]benzonitrile
• 英文别名: 4-[4-[6-(trifluoromethyl)-1H-indol-2-yl]phenoxy]benzonitrile
• CAS: 1162684-46-9
• 化学式: C₂₂H₁₃F₃N₂O
• 分子量: 378.353
• InChiKey: BVKSQJLOBNLYKG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  28
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  48.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4-[4-(6-trifluoromethyl-1H-indol-2-yl)phenoxy]benzonitrile 在 盐酸 、 氨 作用下， 以 乙醇 、 氯仿 、 乙醚 为溶剂， 反应 72.5h， 以70%的产率得到4-(4-(6-(trifluoromethyl)-1H-indol-2-yl)phenoxy)benzimidamide hydrochloride
  参考文献：
  名称：

  Synthesis and Biological Evaluation of Inhibitors of Botulinum Neurotoxin Metalloprotease

  摘要：

  Based on the lead therapeutic agent NSC 240898, a new series of heterocyclic inhibitors of the BoNT serotype A metalloprotease has been generated. Highlights of the synthetic sequences include Sonogashira couplings of polysubstituted building blocks and gold-catalyzed indole formations. Preliminary structure-activity relationship studies afford detailed insights into the steric and electrostatic properties of the pharmacophore of this molecular scaffold.

  DOI：

  10.3987/com-08-s(d)8
• 作为产物：
  描述：

  4-(4-((2-amino-4-(trifluoromethyl)phenyl)ethynyl)phenoxy)benzonitrile 在 三苯基膦氯金 、 silver perchlorate 作用下， 以 二氯甲烷 为溶剂， 反应 14.0h， 以87%的产率得到4-[4-(6-trifluoromethyl-1H-indol-2-yl)phenoxy]benzonitrile
  参考文献：
  名称：

  Synthesis and Biological Evaluation of Inhibitors of Botulinum Neurotoxin Metalloprotease

  摘要：

  Based on the lead therapeutic agent NSC 240898, a new series of heterocyclic inhibitors of the BoNT serotype A metalloprotease has been generated. Highlights of the synthetic sequences include Sonogashira couplings of polysubstituted building blocks and gold-catalyzed indole formations. Preliminary structure-activity relationship studies afford detailed insights into the steric and electrostatic properties of the pharmacophore of this molecular scaffold.

  DOI：

  10.3987/com-08-s(d)8

文献信息

• Synthesis and Biological Evaluation of Inhibitors of Botulinum Neurotoxin Metalloprotease
  作者：Peter Wipf、Chenbo Wang、Julia Widom、Filip Petronijevic、James C. Burnett、Jonathan E. Nuss、Sina Bavari、Rick Gussio

  DOI：10.3987/com-08-s(d)8

  日期：——

  Based on the lead therapeutic agent NSC 240898, a new series of heterocyclic inhibitors of the BoNT serotype A metalloprotease has been generated. Highlights of the synthetic sequences include Sonogashira couplings of polysubstituted building blocks and gold-catalyzed indole formations. Preliminary structure-activity relationship studies afford detailed insights into the steric and electrostatic properties of the pharmacophore of this molecular scaffold.