(4-((3-chloro-4-fluorophenyl)(methyl)amino)thieno[2,3-d]pyrimidin-6-yl)(1-(phenylsulfonyl)-1H-indol-2-yl)methanone | 1355970-21-6

• 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: (4-((3-chloro-4-fluorophenyl)(methyl)amino)thieno[2,3-d]pyrimidin-6-yl)(1-(phenylsulfonyl)-1H-indol-2-yl)methanone
• CAS: 1355970-21-6
• 化学式: C₂₈H₁₈ClFN₄O₃S₂
• 分子量: 577.059
• InChiKey: XAXQOHBBNXTDHQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.67
• 重原子数：
  39.0
• 可旋转键数：
  6.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.04
• 拓扑面积：
  85.16
• 氢给体数：
  0.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  (4-((3-chloro-4-fluorophenyl)(methyl)amino)thieno[2,3-d]pyrimidin-6-yl)(1-(phenylsulfonyl)-1H-indol-2-yl)methanone 在 水 、 sodium hydroxide 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 1.5h， 以74%的产率得到(4-((3-chloro-4-fluorophenyl)(methyl)amino)thieno[2,3-d]pyrimidin-6-yl)(1H-indol-2-yl)methanone
  参考文献：
  名称：

  Novel inhibitors of epidermal growth factor receptor: (4-(Arylamino)-7H-pyrrolo[2,3-d]pyrimidin-6-yl)(1H-indol-2-yl)methanones and (1H-indol-2-yl)(4-(phenylamino)thieno[2,3-d]pyrimidin-6-yl)methanones

  摘要：

  Several members of the quinazoline class of known tyrosine kinase inhibitors are approved anticancer agents, often showing selectivity for receptors of the HER/ErbB-family. Combining structural elements of this class with the bisindolylmethanone-structure led to a series of novel compounds. These compounds inhibited EGFR in the nanomolar range. Moreover, inhibition of EGFR autophosphorylation in intact A431 cells was shown, with IC50 values ranging form 0.3-1 mu M for compound 42, and 0.1-0.3 mu M for 45. In a panel of 42 human tumor cell lines the sensitivity profile of the novel compounds was shown to be similar to that of the quinazoline class of tyrosine kinase inhibitors lapatinib and erlotinib (Tarceva (R)). (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.11.023
• 作为产物：
  描述：

  4-chlorothieno[2,3-d]pyrimidine-6-carbonyl chloride 在 正丁基锂 、 sodium hydride 作用下， 以 四氢呋喃 、 正己烷 、 丁酮 、 mineral oil 为溶剂， 反应 49.58h， 生成 (4-((3-chloro-4-fluorophenyl)(methyl)amino)thieno[2,3-d]pyrimidin-6-yl)(1-(phenylsulfonyl)-1H-indol-2-yl)methanone
  参考文献：
  名称：

  Novel inhibitors of epidermal growth factor receptor: (4-(Arylamino)-7H-pyrrolo[2,3-d]pyrimidin-6-yl)(1H-indol-2-yl)methanones and (1H-indol-2-yl)(4-(phenylamino)thieno[2,3-d]pyrimidin-6-yl)methanones

  摘要：

  Several members of the quinazoline class of known tyrosine kinase inhibitors are approved anticancer agents, often showing selectivity for receptors of the HER/ErbB-family. Combining structural elements of this class with the bisindolylmethanone-structure led to a series of novel compounds. These compounds inhibited EGFR in the nanomolar range. Moreover, inhibition of EGFR autophosphorylation in intact A431 cells was shown, with IC50 values ranging form 0.3-1 mu M for compound 42, and 0.1-0.3 mu M for 45. In a panel of 42 human tumor cell lines the sensitivity profile of the novel compounds was shown to be similar to that of the quinazoline class of tyrosine kinase inhibitors lapatinib and erlotinib (Tarceva (R)). (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.11.023