N-(3-溴苯基)-6,7-二甲氧基-N-甲基-4-喹唑啉胺 | 229476-53-3

• 物质功能分类: 生物化工 - 生化试剂 - 激动剂抑制剂
• 分子结构分类: 有机化合物 - 有机氮化合物
• 中文名称: N-(3-溴苯基)-6,7-二甲氧基-N-甲基-4-喹唑啉胺
• 英文名称: EBE-A22
• 英文别名: N-(3-bromophenyl)-6,7-dimethoxy-N-methylquinazolin-4-amine
• CAS: 229476-53-3
• 化学式: C₁₇H₁₆BrN₃O₂
• 分子量: 374.237
• InChiKey: IPWGDOZPSOZFOD-UHFFFAOYSA-N

物化性质

• 沸点：
  507.3±50.0 °C(Predicted)
• 密度：
  1.446±0.06 g/cm3(Predicted)
• 溶解度：
  DMSO：50mg/mL（133.61 mM）；水：< 0.1 mg/mL（不溶）

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  47.5
• 氢给体数：
  0
• 氢受体数：
  5

安全信息

• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335
• 储存条件：
  -20℃

制备方法与用途

生物活性

EBE-A22是PD 153035的衍生物。虽然PD 153035能够抑制ErbB-1的磷酸化，但EBE-A22不具备这种活性。

反应信息

• 作为产物：
  描述：

  4-[(3-溴苯基)氨基]-6,7-二甲氧基喹啉 、 碘甲烷 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 N-(3-溴苯基)-6,7-二甲氧基-N-甲基-4-喹唑啉胺
  参考文献：
  名称：

  Impact of aryloxy-linked quinazolines: A novel series of selective VEGFR-2 receptor tyrosine kinase inhibitors

  摘要：

  Three series of 6,7-dimethoxyquinazoline derivatives substituted in the 4-position by aniline, N-methylaniline and aryloxy entities, targeting EGFR and VEGFR-2 tyrosine kinases, were designed and synthesized. Pharmacological activities of these compounds have been evaluated for their enzymatic inhibition of VEGFR-2 and EGFR and for their antiproliferative activities on various cancer cell lines. We have studied the impact of the variation in the 4-position substitution of the quinazoline core. Substitution by aryloxy groups led to new compounds which are selective inhibitors of VEGFR-2 enzyme with IC50 values in the nanomolar range in vitro. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.01.137

文献信息

• Impact of aryloxy-linked quinazolines: A novel series of selective VEGFR-2 receptor tyrosine kinase inhibitors
  作者：Antonio Garofalo、Laurence Goossens、Perrine Six、Amélie Lemoine、Séverine Ravez、Amaury Farce、Patrick Depreux

  DOI：10.1016/j.bmcl.2011.01.137

  日期：2011.4

  Three series of 6,7-dimethoxyquinazoline derivatives substituted in the 4-position by aniline, N-methylaniline and aryloxy entities, targeting EGFR and VEGFR-2 tyrosine kinases, were designed and synthesized. Pharmacological activities of these compounds have been evaluated for their enzymatic inhibition of VEGFR-2 and EGFR and for their antiproliferative activities on various cancer cell lines. We have studied the impact of the variation in the 4-position substitution of the quinazoline core. Substitution by aryloxy groups led to new compounds which are selective inhibitors of VEGFR-2 enzyme with IC50 values in the nanomolar range in vitro. (C) 2011 Elsevier Ltd. All rights reserved.