7-(diethylamino)-3-(piperazine-1-carbonyl)-2H-chromen-2-one trifluoroacetate | 1246818-93-8

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 香豆素及其衍生物
• 英文名称: 7-(diethylamino)-3-(piperazine-1-carbonyl)-2H-chromen-2-one trifluoroacetate
• CAS: 1246818-93-8
• 化学式: C₂HF₃O₂*C₁₈H₂₃N₃O₃
• 分子量: 443.423
• InChiKey: XSUWCCZBYZWSQW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.32
• 重原子数：
  31.0
• 可旋转键数：
  4.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  103.09
• 氢给体数：
  2.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  7-(diethylamino)-3-(piperazine-1-carbonyl)-2H-chromen-2-one trifluoroacetate 、 2-(12-bromo-1,2,3,5,6,7-hexahydrochromeno[2,3-f]pyrido[3,2,1-ij]quinolin-4-ium-9-yl)-5-sulfobenzenesulfonate 在 potassium phosphate 作用下， 以 N-甲基吡咯烷酮 为溶剂， 反应 5.0h， 以63%的产率得到
  参考文献：
  名称：

  通过单溴代亚砜染料的亲核胺化快速合成不对称磺基罗丹明

  摘要：

  介绍了一种从不寻常的单溴代亚砜染料和伯胺或仲胺通过直接 SNAr 型反应合成 N 取代不对称磺基罗丹明荧光团的无过渡金属方法。通过快速制备多功能红色罗丹明类似物库，证明了这种“后氨基化”程序的简单性和有效性。这些类似物中的一些配备有反应性手柄并保留起始卤化衍生物的两个水溶性磺酸部分；这使它们成为生物标记应用的理想候选者。

  DOI：

  10.1002/ejoc.201403165
• 作为产物：
  描述：

  4-(二乙氨基)水杨醛 在 吡啶 、 1-羟基苯并三唑 、 苯胺 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 3.17h， 生成 7-(diethylamino)-3-(piperazine-1-carbonyl)-2H-chromen-2-one trifluoroacetate
  参考文献：
  名称：

  Coumarin-based fluorogenic agents and uses thereof for specific protein labelling

  摘要：

  提供了包含与荧光团连接的二马来酰亚胺核的荧光标记试剂，以及其制备方法和用途，用于标记和/或检测特定蛋白靶标。描述了包含具有Formula I结构的化合物的荧光标记试剂及其盐。

  公开号：

  US09701667B2

文献信息

• Rational Design of FRET-Based Ratiometric Chemosensors for in Vitro and in Cell Fluorescence Analyses of Nucleoside Polyphosphates
  作者：Yasutaka Kurishita、Takahiro Kohira、Akio Ojida、Itaru Hamachi

  DOI：10.1021/ja103615z

  日期：2010.9.29

  Ratiometric fluorescence sensing is a useful technique for the precise and quantitative analysis of biological events occurring under complex conditions, such as those inside cells. We report herein the design of new ratiometric chemosensors for nucleoside polyphosphates such as ATP that are based on binding-induced modulation of fluorescence resonance energy transfer (FRET) coupled with a turn-on fluorescence-sensing mechanism. We designed these new FRET-based ratiometric chemosensors by utilizing spectral overlap changes to modulate the FRET efficiency. Introduction of coumarin fluorophores as the FRET donors into a binuclear zinc complex as the FRET acceptor provided the ratiometric chemosensors. These chemosensors exhibited a clear dual-mission signal change upon binding with strong affinity (K-app approximate to 10(6)-10(7) M-1) to nucleoside polyphosphates in aqueous solution, whereas no detectable emission change was observed with monophosphates and phosphodiester species or various other anions. These chemosensors were used for real-time fluorescence monitoring of enzyme reactions such as saccharide synthesis by glycosyltransferase and phosphorylation by protein kinase, both of which involve nucleoside polyphosphates as substrates. The utility of ratiometric sensing by chemosensors was further demonstrated in a fluorescence-imaging study of the nucleoside polyphosphates inside living cells, wherein we ratiometrically visualized the stimulus-responsive concentration change of ATP, an indicator of the cellular energy level.