3-(4-bromo-3,5-dimethyl-1H-pyrrol-2-ylmethylene)-1,3-dihydro-indol-2-one | 856434-66-7

• 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: 3-(4-bromo-3,5-dimethyl-1H-pyrrol-2-ylmethylene)-1,3-dihydro-indol-2-one
• 英文别名: 3-[(4-bromo-3,5-dimethyl-1H-pyrrol-2-yl)methylidene]-1H-indol-2-one
• CAS: 856434-66-7
• 化学式: C₁₅H₁₃BrN₂O
• 分子量: 317.185
• InChiKey: RNZBDLCTBWAQPA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  19
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  44.9
• 氢给体数：
  2
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  3-(4-bromo-3,5-dimethyl-1H-pyrrol-2-ylmethylene)-1,3-dihydro-indol-2-one 在 (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride 、 10% palladium on activated charcoal 、 氢气 、 potassium carbonate 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 水 为溶剂， 反应 1.0h， 生成 3-[[4-(3-aminophenyl)-3,5-dimethyl-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：

  1,3-二氢-3-[(3,5-二甲基-1H-吡咯-2-基)亚甲基]-2H-吲哚-2-酮 在 N-溴代丁二酰亚胺(NBS) 、 过氧化苯甲酰 作用下， 以 四氯化碳 为溶剂， 以1.1 g的产率得到3-(4-bromo-3,5-dimethyl-1H-pyrrol-2-ylmethylene)-1,3-dihydro-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

文献信息

• Novel therapeutic use
  申请人：Bouerat Duvold Maud Elysa Laetitia

  公开号：US20070167488A1

  公开（公告）日：2007-07-19

  Certain oxindole compounds have been found to be effective in experimentally induced autoimmune encephalitis and are therefore suggested for the preparation of a medicament for the prevention, treatment or amelioration of multiple sclerosis, or to delay the onset of or reduce the relapse rate in multiple sclerosis.

  某些恶唑酮化合物已被发现在实验性自身免疫脑炎中具有疗效，因此建议用于制备用于预防、治疗或改善多发性硬化症的药物，或者延迟多发性硬化症的发作或减少复发率。
• Virtual screening and further development of novel ALK inhibitors
  作者：Masako Okamoto、Hirotatsu Kojima、Nae Saito、Takayoshi Okabe、Yoshiaki Masuda、Toshio Furuya、Tetsuo Nagano

  DOI：10.1016/j.bmc.2011.04.008

  日期：2011.5

  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.