2-[[[4-(3-Bromoanilino)quinazolin-6-yl]amino]methyl]benzene-1,4-diol | 828247-13-8

• 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: 2-[[[4-(3-Bromoanilino)quinazolin-6-yl]amino]methyl]benzene-1,4-diol
• CAS: 828247-13-8
• 化学式: C₂₁H₁₇BrN₄O₂
• 分子量: 437.296
• InChiKey: BXPOJEXUKFDGJM-UHFFFAOYSA-N

物化性质

• 熔点：
  231 °C (decomp)(Solv: dichloromethane (75-09-2); methanol (67-56-1))
• 沸点：
  665.5±55.0 °C(Predicted)
• 密度：
  1.624±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  28
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  90.3
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2-[[[4-(3-Bromoanilino)quinazolin-6-yl]amino]methyl]benzene-1,4-diol 在 四丁基高碘酸铵 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 0.03h， 生成 2-[[[4-(3-Bromoanilino)quinazolin-6-yl]amino]methyl]cyclohexa-2,5-diene-1,4-dione 、
  参考文献：
  名称：

  4-Anilinoquinazolines with Lavendustin A subunit as inhibitors of epidermal growth factor receptor tyrosine kinase: syntheses, chemical and pharmacological properties

  摘要：

  4-Anilinoquinazoline derivatives are widely investigated due to their potent epidermal growth factor receptor (EGFR) tyrosine kinase inhibitory activity. Two 4-anilinoquinazolines with Lavendustin A subunit (10a,b) were synthesized and examined for their EGFR tyrosine kinase inhibitory activity as well as their antiproliferative properties on variant human cancer cell lines. Both compounds maintained their EGFR tyrosine kinase inhibitory activity at the 10-7 M level and led to significant growth inhibition in certain leukemia, non-small cell lung cancer (NSCLC). ovarian cancer. renal cancer and breast cancer cell lines with GI(50) values at the 10-6 M level. There could not be observed any notable difference between 10a and lob regarding to their antiproliferative activity. Interestingly, we observed the high tendency of 10a and 10b to include certain solvents. e.g. water. DMF, DMSO, which may be due to the remarkable number of hydrogen accepting/donating groups in 10a and b. An X-ray analysis of 10a including water and DMF illustrates a possible hydrogen bond pattern and could serve as information for preferred receptor (e.g. EGFR tyrosine kinase) binding sites. Finally, we aimed for irreversible EGFR tyrosine kinase inhibitors. The p-quinone derivatives 11a and 11b, which contain a Michael acceptor position according to the irreversible inhibitor CI-1033. Could be derived from the p-hydroquinone derivatives 10a or 10b, respectively, by oxidation. However, due to their instability 11a and 11b could not be obtained in a pure form. (C) 2004 Elsevier SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2004.03.010
• 作为产物：
  描述：

  2-氰基-4-硝基苯胺 在 铁粉 、 dimethylamine borane 、 溶剂黄146 作用下， 以 乙醇 为溶剂， 反应 9.0h， 生成 2-[[[4-(3-Bromoanilino)quinazolin-6-yl]amino]methyl]benzene-1,4-diol
  参考文献：
  名称：

  4-Anilinoquinazolines with Lavendustin A subunit as inhibitors of epidermal growth factor receptor tyrosine kinase: syntheses, chemical and pharmacological properties

  摘要：

  4-Anilinoquinazoline derivatives are widely investigated due to their potent epidermal growth factor receptor (EGFR) tyrosine kinase inhibitory activity. Two 4-anilinoquinazolines with Lavendustin A subunit (10a,b) were synthesized and examined for their EGFR tyrosine kinase inhibitory activity as well as their antiproliferative properties on variant human cancer cell lines. Both compounds maintained their EGFR tyrosine kinase inhibitory activity at the 10-7 M level and led to significant growth inhibition in certain leukemia, non-small cell lung cancer (NSCLC). ovarian cancer. renal cancer and breast cancer cell lines with GI(50) values at the 10-6 M level. There could not be observed any notable difference between 10a and lob regarding to their antiproliferative activity. Interestingly, we observed the high tendency of 10a and 10b to include certain solvents. e.g. water. DMF, DMSO, which may be due to the remarkable number of hydrogen accepting/donating groups in 10a and b. An X-ray analysis of 10a including water and DMF illustrates a possible hydrogen bond pattern and could serve as information for preferred receptor (e.g. EGFR tyrosine kinase) binding sites. Finally, we aimed for irreversible EGFR tyrosine kinase inhibitors. The p-quinone derivatives 11a and 11b, which contain a Michael acceptor position according to the irreversible inhibitor CI-1033. Could be derived from the p-hydroquinone derivatives 10a or 10b, respectively, by oxidation. However, due to their instability 11a and 11b could not be obtained in a pure form. (C) 2004 Elsevier SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2004.03.010