7-[2-(2-aminoethoxy)ethoxy]-N-(4-chloro-2-fluorophenyl)-6-methoxyquinazolin-4-amine | 873301-68-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 英文名称: 7-[2-(2-aminoethoxy)ethoxy]-N-(4-chloro-2-fluorophenyl)-6-methoxyquinazolin-4-amine
• CAS: 873301-68-9
• 化学式: C₁₉H₂₀ClFN₄O₃
• 分子量: 406.844
• InChiKey: CAPGBMXAOBJVQI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  28
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  91.5
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  7-[2-(2-aminoethoxy)ethoxy]-N-(4-chloro-2-fluorophenyl)-6-methoxyquinazolin-4-amine 、 (+)-生物素 4-硝基苯酯 在 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 10.0h， 以94%的产率得到
  参考文献：
  名称：

  Synthesis of a novel biotin-tagged photoaffinity probe for VEGF receptor tyrosine kinases

  摘要：

  A novel biotin-tagged photoaffinity probe was synthesized and evaluated as a vascular endothelial growth factor receptor-2 (VEGFR-2) tyrosine kinase inhibitor. The probe (2) is a potent VEGFR-2 inhibitor with an IC50 value of 7.1 mu M, and inhibits VEGF-induced proliferation in human umbilical vein endothelial cells (HUVEC), with an IC50 value of 40.3 mu M. This probe will be a useful reagent for investigating ligand-protein interactions. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.09.036
• 作为产物：
  描述：

  4-(4-氯-2-氟苯基氨基)-7-羟基-6-甲氧基喹唑啉 在 palladium dihydroxide ammonium hydroxide 、 sodium azide 、 氢气 、 potassium carbonate 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 19.0h， 生成 7-[2-(2-aminoethoxy)ethoxy]-N-(4-chloro-2-fluorophenyl)-6-methoxyquinazolin-4-amine
  参考文献：
  名称：

  Synthesis of a novel biotin-tagged photoaffinity probe for VEGF receptor tyrosine kinases

  摘要：

  A novel biotin-tagged photoaffinity probe was synthesized and evaluated as a vascular endothelial growth factor receptor-2 (VEGFR-2) tyrosine kinase inhibitor. The probe (2) is a potent VEGFR-2 inhibitor with an IC50 value of 7.1 mu M, and inhibits VEGF-induced proliferation in human umbilical vein endothelial cells (HUVEC), with an IC50 value of 40.3 mu M. This probe will be a useful reagent for investigating ligand-protein interactions. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.09.036

文献信息

• Design and synthesis of novel photoaffinity reagents for labeling VEGF receptor tyrosine kinases
  作者：Sun-Young Han、Seo Hyun Choi、Myung Hee Kim、Woo Ghil Lee、Seong Hwan Kim、Yong Ki Min、Bum Tae Kim

  DOI：10.1016/j.tetlet.2006.02.119

  日期：2006.4

  Novel biotin-tagged photoaffinity probes based on a trifunctional tertiary amine scaffold were synthesized and evaluated as vascular endothelial growth factor receptor-2 (VEGFR-2) inhibitors. Probes 3a–c inhibit VEGF induced proliferation in HUVE cells, with IC50 values of 29.7, 33.3, and 37.7 μM, respectively. Moreover, we identified the interaction of 3b with VEGFR-2 in photoaffinity labeling experiment

  合成了基于三功能叔胺支架的新型生物素标记光亲和探针，并将其评估为血管内皮生长因子受体2（VEGFR-2）抑制剂。探针3a – c抑制VEGF诱导的HUVE细胞增殖，IC 50值分别为29.7、33.3和37.7μM 。此外，我们在HUVE细胞的光亲和标记实验中鉴定了3b与VEGFR-2的相互作用。
• Synthesis of a novel biotin-tagged photoaffinity probe for VEGF receptor tyrosine kinases
  作者：Sun-Young Han、Seok-Soon Park、Woo Ghil Lee、Yong Ki Min、Bum Tae Kim

  DOI：10.1016/j.bmcl.2005.09.036

  日期：2006.1

  A novel biotin-tagged photoaffinity probe was synthesized and evaluated as a vascular endothelial growth factor receptor-2 (VEGFR-2) tyrosine kinase inhibitor. The probe (2) is a potent VEGFR-2 inhibitor with an IC50 value of 7.1 mu M, and inhibits VEGF-induced proliferation in human umbilical vein endothelial cells (HUVEC), with an IC50 value of 40.3 mu M. This probe will be a useful reagent for investigating ligand-protein interactions. (c) 2005 Elsevier Ltd. All rights reserved.