2-(7-amino-2-oxo-4-(trifluoromethyl)-1,2-dihydroquinolin-3-yl)-N-(6-(2-bromoacetamido)hexyl)acetamide | 1431329-87-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 2-(7-amino-2-oxo-4-(trifluoromethyl)-1,2-dihydroquinolin-3-yl)-N-(6-(2-bromoacetamido)hexyl)acetamide
• CAS: 1431329-87-1
• 化学式: C₂₀H₂₄BrF₃N₄O₃
• 分子量: 505.335
• InChiKey: HMHDFJUQIWFBCX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.86
• 重原子数：
  31.0
• 可旋转键数：
  10.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  117.08
• 氢给体数：
  4.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  二亚乙基三胺五乙酸二酐 、 2-(7-amino-2-oxo-4-(trifluoromethyl)-1,2-dihydroquinolin-3-yl)-N-(6-(2-bromoacetamido)hexyl)acetamide 以 二甲基亚砜 为溶剂， 反应 0.83h， 生成 2-[2-[bis(carboxymethyl)amino]ethyl-[2-[[2-[[3-[2-[6-[(2-bromoacetyl)amino]hexylamino]-2-oxoethyl]-2-oxo-4-(trifluoromethyl)-1H-quinolin-7-yl]amino]-2-oxoethyl]-(carboxymethyl)amino]ethyl]amino]acetic acid
  参考文献：
  名称：

  New quinolone-based thiol-reactive lanthanide luminescent probes

  摘要：

  Luminescent lanthanide ion complexes are distinguished by unique light emitting properties that enable both highly sensitive detection of lanthanide labels attached to biomolecules and contrast imaging of various micro objects (cells, nanoparticles, etc.). Previously, we synthesized amine-reactive cs124-based luminescent lanthanide chelates with improved brightness and metal retention. Here we report the synthesis of new thiol-reactive derivatives of the same compounds including bromoacetamido-, and maleimido-forms of cs124 and cs124CF(3) fluorophores. Maleimido-compounds displayed exceptional reactivity instantaneously coupling to thiols at physiological conditions at micromolar probes concentrations. Surprisingly, they displayed strong quenching by adjacent maleimido-group, which was completely eliminated after reaction with thiols, thereby enabling their simple detection by monitoring the light emission of the reaction mixture. This reaction can be used for hyper-sensitive determination of biologically important sulphydryl compounds (e.g. glutathione, co-enzyme A, etc.) in time-resolved mode. (C) 2013 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jphotochem.2012.12.008
• 作为产物：
  描述：

  2-(7-amino-2-oxo-4-(trifluoromethyl)-1,2-dihydroquinolin-3-yl)acetic acid 在 N,N-二异丙基乙胺 作用下， 以 二甲基亚砜 为溶剂， 反应 2.58h， 生成 2-(7-amino-2-oxo-4-(trifluoromethyl)-1,2-dihydroquinolin-3-yl)-N-(6-(2-bromoacetamido)hexyl)acetamide
  参考文献：
  名称：

  New quinolone-based thiol-reactive lanthanide luminescent probes

  摘要：

  Luminescent lanthanide ion complexes are distinguished by unique light emitting properties that enable both highly sensitive detection of lanthanide labels attached to biomolecules and contrast imaging of various micro objects (cells, nanoparticles, etc.). Previously, we synthesized amine-reactive cs124-based luminescent lanthanide chelates with improved brightness and metal retention. Here we report the synthesis of new thiol-reactive derivatives of the same compounds including bromoacetamido-, and maleimido-forms of cs124 and cs124CF(3) fluorophores. Maleimido-compounds displayed exceptional reactivity instantaneously coupling to thiols at physiological conditions at micromolar probes concentrations. Surprisingly, they displayed strong quenching by adjacent maleimido-group, which was completely eliminated after reaction with thiols, thereby enabling their simple detection by monitoring the light emission of the reaction mixture. This reaction can be used for hyper-sensitive determination of biologically important sulphydryl compounds (e.g. glutathione, co-enzyme A, etc.) in time-resolved mode. (C) 2013 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jphotochem.2012.12.008