3-((2-aminoethyl)amino)-9,10-dihydro-7H-benzo[de]imidazo[2,1-a]isoquinolin-7-one | 1256844-00-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异喹啉及其衍生物
• 英文名称: 3-((2-aminoethyl)amino)-9,10-dihydro-7H-benzo[de]imidazo[2,1-a]isoquinolin-7-one
• CAS: 1256844-00-4
• 化学式: C₁₆H₁₆N₄O
• 分子量: 280.329
• InChiKey: LCQNETFETDIWPP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.88
• 重原子数：
  21.0
• 可旋转键数：
  3.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  72.41
• 氢给体数：
  2.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  3-((2-aminoethyl)amino)-9,10-dihydro-7H-benzo[de]imidazo[2,1-a]isoquinolin-7-one 、 5-formylcytosine 以 甲醇 为溶剂， 以90%的产率得到5-naphtho-ethyleneimine-2’-deoxycytidine
  参考文献：
  名称：

  荧光染料对DNA中5-甲酰基胞嘧啶的选择性化学标记

  摘要：

  直接标记：可以用含有活性氨基的荧光染料选择性标记DNA中的5-甲酰基胞嘧啶。标记的DNA显示强荧光，可以通过聚丙烯酰胺凝胶电泳（PAGE）和荧光测量（请参见方案）进行检测。这种方法可以将5-甲酰基胞嘧啶与DNA中胞嘧啶的其他甲基化形式区分开。

  DOI：

  10.1002/chem.201300082
• 作为产物：
  描述：

  4-氯-1,8-萘二甲酸酐 、 乙二胺 生成 3-((2-aminoethyl)amino)-9,10-dihydro-7H-benzo[de]imidazo[2,1-a]isoquinolin-7-one
  参考文献：
  名称：

  Synthesis, sensor activity, and logic behavior of a highly water-soluble 9,10-dihydro-7H-imidazo[1,2-b]benz[d,e]isoqionolin-7-one dicarboxylic acid

  摘要：

  The design, synthesis, and sensor activity of a novel highly water-soluble 9,10-dihydro-7H-imidazo[1,2-b] benz[d,e]isoqionolin-7-one derivative are reported. The changes in the photophysical properties of the compound as a function of pH were investigated in 100% aqueous medium. Novel compound manifests ratiometric "off-on-off' pH sensor activity. Due to the two different "off"-states, it is able to execute the logical functions AND and XOR as well as INH and XNOR and as such, to act as a half-adder and a magnitude digital comparator, respectively. The synthesized compound shows excellent selectivity toward protons over the representative metal ions in ammonia/ammonium chloride buffer (pH 10) and HEPES (pH 7.3) solutions. The high water solubility and excellent pH selectivity and sensitivity of the probe may be beneficially for monitoring pH variations in complex samples. (C) 2014 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jphotochem.2014.09.013

文献信息

• The design, synthesis and photophysical properties of two novel 1,8-naphthalimide fluorescent pH sensors based on PET and ICT
  作者：Nikolai I. Georgiev、Vladimir B. Bojinov、Peter S. Nikolov

  DOI：10.1016/j.dyepig.2010.08.004

  日期：2011.3

  The changes in the photophysical properties of two novel yellow green emitting pH chemosensors namely a 1 8-naphthalimide dye and its condensed heterocyclic derivative as a function of pH were investigated in water/ethanol The 1 8-naphthalimide dye displayed on-off pH sensing properties owing to photoinduced electron transfer while its condensed heterocyclic derivative revealed off-on-off pH sensor activity derived from simultaneous photoinduced electron transfer and internal charge transfer In alkaline media the fluorescence of the 1 8-naphthailimide dye was quenched owing to photoinduced electron transfer being disabled in acidic media The pK(a) of the 1 8-naphthailimide dye was 549 which defines the dye as a highly efficient off on switch For the heterocyclic 1 8-naphthalimide derivative two fluorescence quenching processes at different pH were observed one with a pK(a) value of 608 and a second with a pK(a) value of 395 These results indicate that the heterocyclic derivative would be able to act as an efficient off on off fluorescent pH switch (C) 2010 Elsevier Ltd All rights reserved