N⁴-(3-bromophenyl)-N⁶-(4-methoxybenzyl)quinazoline-4,6-diamine | 1354795-66-6

• 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: N⁴-(3-bromophenyl)-N⁶-(4-methoxybenzyl)quinazoline-4,6-diamine
• 英文别名: N6-(4-methoxybenzyl)-N4-(3-bromophenyl)quinazoline-4,6-diamine；4-N-(3-bromophenyl)-6-N-[(4-methoxyphenyl)methyl]quinazoline-4,6-diamine
• CAS: 1354795-66-6
• 化学式: C₂₂H₁₉BrN₄O
• 分子量: 435.323
• InChiKey: RJXXTGDGSWPIOV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  28
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  59.1
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  2-氰基-4-硝基苯胺 在 sodium tetrahydroborate 、 铁粉 、 溶剂黄146 作用下， 以 乙醇 、 水 为溶剂， 反应 2.0h， 生成 N⁴-(3-bromophenyl)-N⁶-(4-methoxybenzyl)quinazoline-4,6-diamine
  参考文献：
  名称：

  Design and synthesis of 4,6-substituted-(diaphenylamino)quinazolines as potent EGFR inhibitors with antitumor activity

  摘要：

  A type of novel 4,6-substituted-(diaphenylamino)quinazolines, which designed based on the 4-(phenylamino)quinazoline moiety, have been discovered as potential EGFR inhibitors. These compounds displayed good antiproliferative activity and EGFR-TK inhibitory activity. Especially, 4-((4-(3-bromophenylamino)quinazolin-6-ylamino)methyl)phenol (5b), showed the most potent inhibitory activity (IC(50) = 0.28 mu M for Hep G2, IC(50) = 0.59 mu Mfor A16-F10 and IC(50) = 0.87 mu M for EGFR) and effectively induces apoptosis in a dose-dependent manner in the Hep G2 cell line. Molecular docking of 5b into EGFR TK active site was also performed. This inhibitor nicely fitting the active site might well explain its excellent inhibitory activity. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.10.085

文献信息

• Design and synthesis of 4,6-substituted-(diaphenylamino)quinazolines as potent EGFR inhibitors with antitumor activity
  作者：Huan-Qiu Li、Dong-Dong Li、Xiang Lu、Yun-Yun Xu、Hai-Liang Zhu

  DOI：10.1016/j.bmc.2011.10.085

  日期：2012.1

  A type of novel 4,6-substituted-(diaphenylamino)quinazolines, which designed based on the 4-(phenylamino)quinazoline moiety, have been discovered as potential EGFR inhibitors. These compounds displayed good antiproliferative activity and EGFR-TK inhibitory activity. Especially, 4-((4-(3-bromophenylamino)quinazolin-6-ylamino)methyl)phenol (5b), showed the most potent inhibitory activity (IC(50) = 0.28 mu M for Hep G2, IC(50) = 0.59 mu Mfor A16-F10 and IC(50) = 0.87 mu M for EGFR) and effectively induces apoptosis in a dose-dependent manner in the Hep G2 cell line. Molecular docking of 5b into EGFR TK active site was also performed. This inhibitor nicely fitting the active site might well explain its excellent inhibitory activity. (C) 2011 Elsevier Ltd. All rights reserved.