4-(5'-ethynylsalicylaldehyde)-N-butyl-1,8-naphthalimides | 1241374-43-5

• 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: 4-(5'-ethynylsalicylaldehyde)-N-butyl-1,8-naphthalimides
• 英文别名: 5-[2-(2-Butyl-1,3-dioxobenzo[de]isoquinolin-6-yl)ethynyl]-2-hydroxybenzaldehyde
• CAS: 1241374-43-5
• 化学式: C₂₅H₁₉NO₄
• 分子量: 397.43
• InChiKey: GWWAVCIENHXTNW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  30
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.16
• 拓扑面积：
  74.7
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-(5'-ethynylsalicylaldehyde)-N-butyl-1,8-naphthalimides 、 苯甲酰肼 以 乙醇 为溶剂， 反应 12.0h， 以58%的产率得到
  参考文献：
  名称：

  1,8-Naphthalimide-based ‘turn-on’ fluorescent sensor for the detection of zinc ion in aqueous media and its applications for bioimaging

  摘要：

  A 1,8-naphthalimide derivative (1) was intentionally designed and synthesized as a new turn-on fluorescent probe for the detection of zinc ion with high selectivity over other metal ions at pH 7.4 in aqueous media (CH3CN/HEPES, V/V=6:4). The reaction mechanism is attributed to the replacement of the protons of the O-H groups by zinc ion at the binding site and production of fluorescence which is blocked in the photo-induced electron transfer (PET) process. Remarkable enhancement of up to 13-fold in fluorescence intensity with a 38 nm red-shift was achieved in the detection of zinc ion. Compound 1 was successfully applied to the fluorescence imaging of zinc ion, with a fluorescence emission color produced in the cell nucleus different from that produced in the cytoplasm, in A549, BEAS-2B, CHO, Hela, and HepG2 cells. Furthermore, cytokinesis-block micronucleus (CBMN) assay was carried out in CHO cells using 1 and zinc ion as the imaging agents, showing that the 1-Zn2+ agent is a nucleic acid selective stain, which could be applied in MN assays in different kinds of cell lines. Crown Copyright (C) 2013 Published by Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2013.04.045
• 作为产物：
  描述：

  N-正丁基-1,8-萘二甲酰亚胺 、 5-乙炔基-2-羟基苯甲醛 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 12.0h， 生成 4-(5'-ethynylsalicylaldehyde)-N-butyl-1,8-naphthalimides
  参考文献：
  名称：

  1,8-Naphthalimide-based visible colorimetric sensor for the selective sensing of fluoride, acetate and hydroxyl anions

  摘要：

  A highly selective and sensitive calorimetric signal-responding anion-sensor 1, based on 1,8-naphthalimide, was prepared and spectroscopically characterized. Strong visible colorimetric changes in 1 were observed only in the presence of fluoride (yellow-to-red color change), acetate (yellow-to-orange color change) and hydroxyl (yellow-to-brown color change) anions in DMSO. In the UV-Vis spectroscopy titration of F-, two different processes were observed as the concentration of F- increased. In the lower concentration of F-, hydrogen-bond interactions were formed in the first process. The second process of the spectral changes, in the higher concentration of F-, was attributed to the deprotonation of the hydroxyl moiety in the binding group, which was associated with the enhancement in the push-pull effect of the internal charge-transfer transition. The commonly competing Cl-, Br-, I-, ClO4, PF6, HSO4 and H2PO4 ions induced none or relatively negligible optical perturbations in the UV-Vis spectral analyses. The present naked-eye detection system provides a simple and rapid method for the detection of fluoride, acetate and hydroxyl anions without interferences from other halide anions or common anions, including ClO4, PF6, HSO4 and H2PO4. (C) 2013 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jfluchem.2013.11.002

文献信息

• Naphthalimide Modified Rhodamine Derivative: Ratiometric and Selective Fluorescent Sensor for Cu²⁺ Based on Two Different Approaches
  作者：Jun Feng Zhang、Ying Zhou、Juyoung Yoon、Youngmee Kim、Sung Jin Kim、Jong Seung Kim

  DOI：10.1021/ol101535s

  日期：2010.9.3

  A new rhodamine-based derivative bearing a 1,8-naphthalimide group (1) was synthesized as a dual-mode Cu2+-selective sensor via the rhodamine ring-opening approach and ratiometric displacement. A colorimetric and "off on" signal for Cu2+ through rhodamine ring opening in 1 and ratiometric fluorescent signal output when Cu2+ displaces the bound Zn2+ in the 1-Zn2+ complex can be observed.