[4-(4-Chloroanilino)quinazolin-6-yl]urea | 1428064-22-5

• 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: [4-(4-Chloroanilino)quinazolin-6-yl]urea
• 英文别名: [4-(4-chloroanilino)quinazolin-6-yl]urea
• CAS: 1428064-22-5
• 化学式: C₁₅H₁₂ClN₅O
• 分子量: 313.746
• InChiKey: YDZATYFCHVJGEI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  92.9
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  2-氰基-4-硝基苯胺 在 ammonium hydroxide 、 sodium dithionite 、 溶剂黄146 作用下， 以 水 为溶剂， 反应 6.0h， 生成 [4-(4-Chloroanilino)quinazolin-6-yl]urea
  参考文献：
  名称：

  Design, synthesis and in vitro anti-proliferative activity of 4,6-quinazolinediamines as potent EGFR-TK inhibitors

  摘要：

  4-Anilino-6-substituted-quinazolines were designed, synthesized and evaluated for EGFR-TK and tumor growth inhibitory activities. The target compounds were designed with enamine ester or urea moieties appended at the C-6 of quinazoline as additional hydrogen bond acceptor functions. Most of the synthesized compounds displayed potent EGFR-TK inhibitory activity at 10 mu M and the 6-ureido-anilinoquinazoline derivative 7a showed IC50 value of 0.061 mu M. Moreover, six compounds were tested by National Cancer Institute (NCI), USA for their anti-proliferative activity at 10 mu M in full NCI 60 cell panel. Compound 7a was further assayed for five dose molar ranges in full NCI 60 cell panel and exhibited remarkable growth inhibitory activity pattern against Non-Small Cell Lung Cancer EKVX (GI(50) = 037 mu M), NCI-H322M (GI(50) = 0.36 mu M), Renal Cancer A498 (GI(50) = 0.46 mu M), TK-10 (GI(50) = 0.99 mu M) and Breast Cancer MDA-MB-468 (GI(50) = 1.096 mu M) which are of high EGFR expression. Docking study was performed for the active compounds into ATP binding site of EGFR-TK which showed similar binding mode to gefitinib and additional binding with Cys-773 at the gatekeeper of EGFR-TK enzyme. (C) 2012 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2012.10.017

文献信息

• Design, synthesis and in vitro anti-proliferative activity of 4,6-quinazolinediamines as potent EGFR-TK inhibitors
  作者：Samar Mowafy、Nahla A. Farag、Khaled A.M. Abouzid

  DOI：10.1016/j.ejmech.2012.10.017

  日期：2013.3

  4-Anilino-6-substituted-quinazolines were designed, synthesized and evaluated for EGFR-TK and tumor growth inhibitory activities. The target compounds were designed with enamine ester or urea moieties appended at the C-6 of quinazoline as additional hydrogen bond acceptor functions. Most of the synthesized compounds displayed potent EGFR-TK inhibitory activity at 10 mu M and the 6-ureido-anilinoquinazoline derivative 7a showed IC50 value of 0.061 mu M. Moreover, six compounds were tested by National Cancer Institute (NCI), USA for their anti-proliferative activity at 10 mu M in full NCI 60 cell panel. Compound 7a was further assayed for five dose molar ranges in full NCI 60 cell panel and exhibited remarkable growth inhibitory activity pattern against Non-Small Cell Lung Cancer EKVX (GI(50) = 037 mu M), NCI-H322M (GI(50) = 0.36 mu M), Renal Cancer A498 (GI(50) = 0.46 mu M), TK-10 (GI(50) = 0.99 mu M) and Breast Cancer MDA-MB-468 (GI(50) = 1.096 mu M) which are of high EGFR expression. Docking study was performed for the active compounds into ATP binding site of EGFR-TK which showed similar binding mode to gefitinib and additional binding with Cys-773 at the gatekeeper of EGFR-TK enzyme. (C) 2012 Elsevier Masson SAS. All rights reserved.