2-[4-(3,4-diaminophenoxy)phenyl]-N-(2-fluoro-5-trifluoromethylphenyl)acetamide | 948313-34-6

• 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: 2-[4-(3,4-diaminophenoxy)phenyl]-N-(2-fluoro-5-trifluoromethylphenyl)acetamide
• 英文别名: 2-[4-(3,4-diaminophenoxy)phenyl]-N-[2-fluoro-5-(trifluoromethyl)phenyl]acetamide
• CAS: 948313-34-6
• 化学式: C₂₁H₁₇F₄N₃O₂
• 分子量: 419.378
• InChiKey: RXUCJDVDJSTUBL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  30
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  90.4
• 氢给体数：
  3
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  2-[4-(3,4-diaminophenoxy)phenyl]-N-(2-fluoro-5-trifluoromethylphenyl)acetamide 、 1,3-二羧甲基-2-甲基-2-硫代异脲 以 乙醇 为溶剂， 生成 methyl N-{6-[4-({[2-fluoro-5-(trifluoromethyl)phenyl]carbamoyl}methyl)phenoxy]-1H-1,3-benzodiazol-2-yl}carbamate
  参考文献：
  名称：

  Discovery of Novel Benzimidazoles as Potent Inhibitors of TIE-2 and VEGFR-2 Tyrosine Kinase Receptors

  摘要：

  We herein disclose a novel chemical series of benzimidazole-ureas as inhibitors of VEGFR-2 and TIE-2 kinase receptors, both of which are implicated in angiogenesis. Structure-activity relationship (SAR) studies elucidated a critical role for the NI nitrogen of both the benzimidazole (segment E) and urea (segment B) moieties. The SAR results were also supported by the X-ray crystallographic elucidation of the role of the NI nitrogen and the urea moiety when the benzimidazole-urea compounds were bound to the VEGFR-2 enzyme. The left side phenyl ring (segment A) occupies the backpocket where a 3-hydrophobic substituent was favored for TIE-2 activity.

  DOI：

  10.1021/jm0611051
• 作为产物：
  描述：

  对羟基苯乙酸 在 palladium on activated charcoal 氢气 、 sodium hydride 、 1-羟基苯并三唑 、 O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate 、 三乙胺 作用下， 以 乙醇 、 二甲基亚砜 、 N,N-二甲基甲酰胺 为溶剂， 反应 0.33h， 生成 2-[4-(3,4-diaminophenoxy)phenyl]-N-(2-fluoro-5-trifluoromethylphenyl)acetamide
  参考文献：
  名称：

  Discovery of Novel Benzimidazoles as Potent Inhibitors of TIE-2 and VEGFR-2 Tyrosine Kinase Receptors

  摘要：

  We herein disclose a novel chemical series of benzimidazole-ureas as inhibitors of VEGFR-2 and TIE-2 kinase receptors, both of which are implicated in angiogenesis. Structure-activity relationship (SAR) studies elucidated a critical role for the NI nitrogen of both the benzimidazole (segment E) and urea (segment B) moieties. The SAR results were also supported by the X-ray crystallographic elucidation of the role of the NI nitrogen and the urea moiety when the benzimidazole-urea compounds were bound to the VEGFR-2 enzyme. The left side phenyl ring (segment A) occupies the backpocket where a 3-hydrophobic substituent was favored for TIE-2 activity.

  DOI：

  10.1021/jm0611051