6-(4-dimethylaminostyryl)-N-benzylquinazolin-4-amine | 1399854-61-5

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: 6-(4-dimethylaminostyryl)-N-benzylquinazolin-4-amine
• 英文别名: N-benzyl-6-[2-[4-(dimethylamino)phenyl]ethenyl]quinazolin-4-amine
• CAS: 1399854-61-5
• 化学式: C₂₅H₂₄N₄
• 分子量: 380.492
• InChiKey: KPIQHODXSDMYLR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.48
• 重原子数：
  29.0
• 可旋转键数：
  6.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  41.05
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为产物：
  描述：

  6-iodo-N-(phenylmethyl)-4-quinazolinamine 、 4-二甲基氨基苯乙烯 在 tris-(dibenzylideneacetone)dipalladium(0) 、 三叔丁基膦 、 caesium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 以12%的产率得到6-(4-dimethylaminostyryl)-N-benzylquinazolin-4-amine
  参考文献：
  名称：

  A fluorescent reporter of ATP binding-competent receptor kinases

  摘要：

  ERBB receptor kinases play a crucial role in normal development and cancer malignancies. A broad range of modifications creates receptor subpopulations with distinct functional properties in live cells. Their apparent activation state, typically assayed by tyrosine phosphorylation of substrates, reflects a complex equilibrium of competing reactions. With the aim of developing optical tools to investigate ERBB populations and their state of activation, we have synthesized a fluorescent 'turn-on' probe, DMAQ, targeting the ERBB ATP binding pocket. Upon binding, probe emission increases due to the hydrophobic environment and restricted geometry of the ERBB2 kinase domain, facilitating the analysis of receptor states at low occupancy and without the removal of unbound probes. Cellular ERBB2 autophosphorylation is inhibited with saturation kinetics that correlate with the increase in probe fluorescence. Thus, DMAQ is an example of a new generation of 'turn-on' probes with potential applications in querying receptor kinase populations both in vitro and in live cells. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.07.034

文献信息

• A fluorescent reporter of ATP binding-competent receptor kinases
  作者：Renaud Sicard、Jyothi Dhuguru、Wenjun Liu、Nirav Patel、Ralf Landgraf、James N. Wilson

  DOI：10.1016/j.bmcl.2012.07.034

  日期：2012.9

  ERBB receptor kinases play a crucial role in normal development and cancer malignancies. A broad range of modifications creates receptor subpopulations with distinct functional properties in live cells. Their apparent activation state, typically assayed by tyrosine phosphorylation of substrates, reflects a complex equilibrium of competing reactions. With the aim of developing optical tools to investigate ERBB populations and their state of activation, we have synthesized a fluorescent 'turn-on' probe, DMAQ, targeting the ERBB ATP binding pocket. Upon binding, probe emission increases due to the hydrophobic environment and restricted geometry of the ERBB2 kinase domain, facilitating the analysis of receptor states at low occupancy and without the removal of unbound probes. Cellular ERBB2 autophosphorylation is inhibited with saturation kinetics that correlate with the increase in probe fluorescence. Thus, DMAQ is an example of a new generation of 'turn-on' probes with potential applications in querying receptor kinase populations both in vitro and in live cells. (C) 2012 Elsevier Ltd. All rights reserved.