3-[[3-(4-aminophenyl)-5-methyl-1H-pyrrol-2-yl]methylene]-1,3-dihydro-2H-indol-2-one | 1312226-30-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: 3-[[3-(4-aminophenyl)-5-methyl-1H-pyrrol-2-yl]methylene]-1,3-dihydro-2H-indol-2-one
• 英文别名: 3-[[3-(4-aminophenyl)-5-methyl-1H-pyrrol-2-yl]methylidene]-1H-indol-2-one
• CAS: 1312226-30-4
• 化学式: C₂₀H₁₇N₃O
• 分子量: 315.374
• InChiKey: PRKMBPQYMVXIKY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.07
• 重原子数：
  24.0
• 可旋转键数：
  2.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  70.91
• 氢给体数：
  3.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  3-[[3-(4-aminophenyl)-5-methyl-1H-pyrrol-2-yl]methylene]-1,3-dihydro-2H-indol-2-one 、 2-溴乙胺氢溴酸盐 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 3.5h， 以60 mg的产率得到3-[[3-[4-[(2-aminoethyl)amino]phenyl]-5-methyl-1H-pyrrol-2-yl]methylene]-1,3-dihydro-2H-indol-2-one
  参考文献：
  名称：

  Virtual screening and further development of novel ALK inhibitors

  摘要：

  Anaplastic lymphoma kinase (ALK) has been in the spotlight in recent years as a promising new target for therapy of non-small-cell lung cancer (NSCLC). Since the identification of the echinoderm microtubule-associated protein-like 4 (EML4)-ALK fusion gene in some NSCLC patients was reported in 2007, various research groups have been seeking ALK inhibitors. Above all, crizotinib (PF-02341066) has been under clinical trial, and its therapeutic efficacy of inhibiting ALK in NSCLC has been reported. Among anticancer drugs, drug resistance appears frequently necessitating various kinds of inhibitors. We identified novel ALK inhibitors by virtual screening from the public chemical library collected by the Chemical Biology Research Initiative (CBRI) at the University of Tokyo, and inhibitors that are more potent were developed. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.04.008
• 作为产物：
  描述：

  对硝基苯甲醛 在 哌啶 、 10% palladium on activated charcoal 、 ammonium acetate 、 氢气 、 sodium methylate 、 溶剂黄146 、 三氟乙酸 、 三氯氧磷 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 3.83h， 生成 3-[[3-(4-aminophenyl)-5-methyl-1H-pyrrol-2-yl]methylene]-1,3-dihydro-2H-indol-2-one
  参考文献：
  名称：

  Virtual screening and further development of novel ALK inhibitors

  摘要：

  Anaplastic lymphoma kinase (ALK) has been in the spotlight in recent years as a promising new target for therapy of non-small-cell lung cancer (NSCLC). Since the identification of the echinoderm microtubule-associated protein-like 4 (EML4)-ALK fusion gene in some NSCLC patients was reported in 2007, various research groups have been seeking ALK inhibitors. Above all, crizotinib (PF-02341066) has been under clinical trial, and its therapeutic efficacy of inhibiting ALK in NSCLC has been reported. Among anticancer drugs, drug resistance appears frequently necessitating various kinds of inhibitors. We identified novel ALK inhibitors by virtual screening from the public chemical library collected by the Chemical Biology Research Initiative (CBRI) at the University of Tokyo, and inhibitors that are more potent were developed. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.04.008