2-[bis(2-ethylsulfanylethyl)amino]-N-quinolin-8-ylacetamide | 1415107-29-7

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 2-[bis(2-ethylsulfanylethyl)amino]-N-quinolin-8-ylacetamide
• CAS: 1415107-29-7
• 化学式: C₁₉H₂₇N₃OS₂
• 分子量: 377.575
• InChiKey: CPHWBICTDXULEI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  25
• 可旋转键数：
  11
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  95.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  zinc perchlorate 、 2-[bis(2-ethylsulfanylethyl)amino]-N-quinolin-8-ylacetamide 以 甲醇 为溶剂， 生成
  参考文献：
  名称：

  A selective and sensitive fluorescence probe for imaging endogenous zinc in living cells

  摘要：

  A carboxamidoquinoline-based fluorescent Zn2+ probe 1 containing N/S/S heteroatoms as a receptor was designed and readily synthesized, which was featured by the Zn2+-induced red-shift of emission (45 nm) based on internal charge transfer (ICT) in an aqueous HEPES buffer (pH=7.4). Moreover, spectroscopic studies indicated that the composition of the complex 1-Zn2+ was 1:1, which was also confirmed by X-ray crystallography. In addition, H-1 NMR titration experiment suggested that probe 1 transformed from the amide tautomer to imidic acid tautomer after binding with Zn2+. The binding of zinc with 1 was easily reversed by addition of N,N,N',N'-tetrakis(2-picolyl)ethylenediamine (TPEN) or EDTA. Furthermore, probe 1 was successfully applied to image both exogenous and endogenous zinc in living HeLa cells. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2012.11.007
• 作为产物：
  描述：

  N1-(8-喹啉基)-2-氯乙酰胺 、 N,N-bis(2-(ethylthio)ethyl)amine 在 N,N-二异丙基乙胺 、 potassium iodide 作用下， 以 乙腈 为溶剂， 反应 10.5h， 以79%的产率得到2-[bis(2-ethylsulfanylethyl)amino]-N-quinolin-8-ylacetamide
  参考文献：
  名称：

  A selective and sensitive fluorescence probe for imaging endogenous zinc in living cells

  摘要：

  A carboxamidoquinoline-based fluorescent Zn2+ probe 1 containing N/S/S heteroatoms as a receptor was designed and readily synthesized, which was featured by the Zn2+-induced red-shift of emission (45 nm) based on internal charge transfer (ICT) in an aqueous HEPES buffer (pH=7.4). Moreover, spectroscopic studies indicated that the composition of the complex 1-Zn2+ was 1:1, which was also confirmed by X-ray crystallography. In addition, H-1 NMR titration experiment suggested that probe 1 transformed from the amide tautomer to imidic acid tautomer after binding with Zn2+. The binding of zinc with 1 was easily reversed by addition of N,N,N',N'-tetrakis(2-picolyl)ethylenediamine (TPEN) or EDTA. Furthermore, probe 1 was successfully applied to image both exogenous and endogenous zinc in living HeLa cells. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2012.11.007

文献信息

• A selective and sensitive fluorescence probe for imaging endogenous zinc in living cells
  作者：Liangwei Zhang、Dongzhu Duan、Xuemei Cui、Jinyu Sun、Jianguo Fang

  DOI：10.1016/j.tet.2012.11.007

  日期：2013.1

  A carboxamidoquinoline-based fluorescent Zn2+ probe 1 containing N/S/S heteroatoms as a receptor was designed and readily synthesized, which was featured by the Zn2+-induced red-shift of emission (45 nm) based on internal charge transfer (ICT) in an aqueous HEPES buffer (pH=7.4). Moreover, spectroscopic studies indicated that the composition of the complex 1-Zn2+ was 1:1, which was also confirmed by X-ray crystallography. In addition, H-1 NMR titration experiment suggested that probe 1 transformed from the amide tautomer to imidic acid tautomer after binding with Zn2+. The binding of zinc with 1 was easily reversed by addition of N,N,N',N'-tetrakis(2-picolyl)ethylenediamine (TPEN) or EDTA. Furthermore, probe 1 was successfully applied to image both exogenous and endogenous zinc in living HeLa cells. (C) 2012 Elsevier Ltd. All rights reserved.