N-(2-allyl-1,3-dioxo-2,3-dihydro-1H-benzo[de]isoquinolin-6-yl)-2-chloroacetamide | 188610-39-1

• 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: N-(2-allyl-1,3-dioxo-2,3-dihydro-1H-benzo[de]isoquinolin-6-yl)-2-chloroacetamide
• 英文别名: 2-chloro-N-(1,3-dioxo-2-prop-2-enylbenzo[de]isoquinolin-6-yl)acetamide
• CAS: 188610-39-1
• 化学式: C₁₇H₁₃ClN₂O₃
• 分子量: 328.755
• InChiKey: ACMGTWJXZIXPQQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  66.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-(2-allyl-1,3-dioxo-2,3-dihydro-1H-benzo[de]isoquinolin-6-yl)-2-chloroacetamide 、 二甲基吡啶胺 在 N,N-二异丙基乙胺 、 potassium iodide 作用下， 以 乙腈 为溶剂， 反应 10.0h， 以55%的产率得到N-(2-allyl-1,3-dioxo-2,3-dihydro-1H-benzo[de]isoquinolin-6-yl)-2-(bis(pyridin-2-ylmethyl)amino)acetamide
  参考文献：
  名称：

  Synthesis and characterization of new selective Zn2+ fluorescent probes for functionalization: in vitro Cell imaging applications

  摘要：

  Herein the synthesis and characterization of new, lipophilic highly Zn2+-selective fluorescent probes are reported. High affinity for zinc (K-d 1.1-8.0 nM) over other biologically relevant metals and mixtures of metals was observed. Excitation at 360 nm afforded an emission spectrum with maximum at 530 nm for the zinc bound complex. The linear relationship between fluorescence intensity and zinc concentration indicates that FZnA-probes can be used for quantification. The probes have been synthesized in 28-45% overall yield and the feasibility for further functionalization with biologically relevant side chains has been demonstrated. In vitro studies using PC12 cells and 10 mu M of one of the novel probes (FZnA-Ada) visualized endogenous labile Zn2+ after 45 min incubation time. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2013.07.049
• 作为产物：
  描述：

  4-氨基-1,8-萘胺 在 4-二甲氨基吡啶 、 sodium methylate 作用下， 以 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 8.17h， 生成 N-(2-allyl-1,3-dioxo-2,3-dihydro-1H-benzo[de]isoquinolin-6-yl)-2-chloroacetamide
  参考文献：
  名称：

  Synthesis and characterization of new selective Zn2+ fluorescent probes for functionalization: in vitro Cell imaging applications

  摘要：

  Herein the synthesis and characterization of new, lipophilic highly Zn2+-selective fluorescent probes are reported. High affinity for zinc (K-d 1.1-8.0 nM) over other biologically relevant metals and mixtures of metals was observed. Excitation at 360 nm afforded an emission spectrum with maximum at 530 nm for the zinc bound complex. The linear relationship between fluorescence intensity and zinc concentration indicates that FZnA-probes can be used for quantification. The probes have been synthesized in 28-45% overall yield and the feasibility for further functionalization with biologically relevant side chains has been demonstrated. In vitro studies using PC12 cells and 10 mu M of one of the novel probes (FZnA-Ada) visualized endogenous labile Zn2+ after 45 min incubation time. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2013.07.049

文献信息

• Synthesis and characterization of new selective Zn2+ fluorescent probes for functionalization: in vitro Cell imaging applications
  作者：Ove Alexander Høgmoen Åstrand、Lars Peter Engeset Austdal、Ragnhild E. Paulsen、Trond Vidar Hansen、Pål Rongved

  DOI：10.1016/j.tet.2013.07.049

  日期：2013.10

  Herein the synthesis and characterization of new, lipophilic highly Zn2+-selective fluorescent probes are reported. High affinity for zinc (K-d 1.1-8.0 nM) over other biologically relevant metals and mixtures of metals was observed. Excitation at 360 nm afforded an emission spectrum with maximum at 530 nm for the zinc bound complex. The linear relationship between fluorescence intensity and zinc concentration indicates that FZnA-probes can be used for quantification. The probes have been synthesized in 28-45% overall yield and the feasibility for further functionalization with biologically relevant side chains has been demonstrated. In vitro studies using PC12 cells and 10 mu M of one of the novel probes (FZnA-Ada) visualized endogenous labile Zn2+ after 45 min incubation time. (C) 2013 Elsevier Ltd. All rights reserved.