2-(2-(dimethylamino)ethyl)-6-((2-(dimethylamino)ethyl)-amino)-1H-benzo[de]isoquinoline-1,3(2H)-dione | 1072878-91-1

• 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: 2-(2-(dimethylamino)ethyl)-6-((2-(dimethylamino)ethyl)-amino)-1H-benzo[de]isoquinoline-1,3(2H)-dione
• 英文别名: 2-[2-(Dimethylamino)ethyl]-6-[2-(dimethylamino)ethylamino]benzo[de]isoquinoline-1,3-dione
• CAS: 1072878-91-1
• 化学式: C₂₀H₂₆N₄O₂
• 分子量: 354.452
• InChiKey: ABKVCQHPAOLOSS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  26
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  55.9
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-(2-(dimethylamino)ethyl)-6-((2-(dimethylamino)ethyl)-amino)-1H-benzo[de]isoquinoline-1,3(2H)-dione 生成 2-[2-(dimethylamino)ethyl]-6-{[2-(dimethylamino)ethyl]-amino}-1H-benzo[de]isoquinoline-1,3(2H)-dione hydrochloride
  参考文献：
  名称：

  Design, synthesis, and biological evaluation of new mitonafide derivatives as potential antitumor drugs

  摘要：

  A series of potential DNA-binding antitumor agents, 2-[omega-(alkylamino) alkyl]-6-{[omega-(alkylamino) alkyl] amino}-1H-benzo[de] isoquinolin-1,3(2H)-diones and 1,7-bis{6-[(omega-(dimethylamino) alkyl) amino]-1,3dioxo-1H-benzo[de] isoquinolin-2(3H)-yl}-4-methyl-4-azaheptanes, have been prepared as mitonafide derivatives. Their DNA-binding ability and cytotoxic activity have been evaluated. Some of the target compounds have shown high DNA affinity as well as relevant cytotoxic properties. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2008.08.027
• 作为产物：
  描述：

  4-硝基-1,8-萘醛酸酐 、 N,N-二甲基乙二胺 以 N,N-二甲基甲酰胺 为溶剂， 反应 8.0h， 以75%的产率得到2-(2-(dimethylamino)ethyl)-6-((2-(dimethylamino)ethyl)-amino)-1H-benzo[de]isoquinoline-1,3(2H)-dione
  参考文献：
  名称：

  Highly Selective and Sensitive Detection of Fe3+ by 1,8-Naphthalimide-Based Fluorescent Sensors

  摘要：

  报道了通过两种基于1,8-萘酰亚胺的荧光传感器对Fe3+的高度选择性和敏感检测，分别为2-(2-(二甲氨基)乙基)-6-((2-(二甲氨基)乙基)氨基)-1H-苯并[de]异喹啉-1,3(2H)-二酮（MMN）和2-(2-(二乙氨基)乙基)-6-((2-(二乙氨基)乙基)氨基)-1H-苯并[de]异喹啉-1,3(2H)-二酮（EEN）在N,N-二甲基甲酰胺中的表现。MMN和EEN的荧光强度因Fe3+离子显著增强，响应时间不足1秒。传感器的最大荧光强度在线性范围内与Fe3+浓度（10-100 μM）成正比。结合化学计量表明Fe3+与传感器之间形成2:1的复合物，MMN和EEN的检测限分别为180和310 nM。大量生物相关离子对检测没有明显干扰。

  DOI：

  10.14233/ajchem.2013.14344

文献信息

• Aggregation-induced emission enhancement characteristics of naphthalimide derivatives and their applications in cell imaging
  作者：Hsin-Hung Lin、Yung-Chieh Chan、Jyun-Wei Chen、Cheng-Chung Chang

  DOI：10.1039/c0jm02942d

  日期：——

  Novel naphthalimide derivatives (NIM) with donor–acceptor architecture were successfully constructed and their unique fluorescent properties were investigated. In particular, the fluorescence intensities of 4-methoxystyrene substituted NIM-1 were solvent independent and its quantum yields varied from 0.4 in toluene to 0.52 in MeOH. However, 4-(N,N-diphenylamino) styrene substituted NIM-2 and 4-nitrostyrene substituted NIM-3 exhibited low luminescence in dilute solutions but were efficiently fluorescent under conditions of molecular aggregation. NIM-2 showed strong solid fluorescence with a longer wavelength emission and larger Stokes shift. In addition, NIM-3 showed unexpected blue-green fluorescence due to the formation of fluorescent organic nanoparticles (FONs) under mixed solution. These two cases were ascribed to the aggregation-induced enhanced emission (AIEE) effects and which can also reasonably explain the bright cellular images observed when cells were incubated with NIM-2 and NIM-3. Furthermore, compound NIM-2 can be used to recognize cancer cells owing to its subcellular behaviour.

  具有供体–受体结构的萘酞亚胺类衍生物（NIM）成功合成，并研究了其独特的荧光特性。其中，4-甲氧基苯乙烯取代的NIM-1的荧光强度与溶剂无关，量子产率在甲苯中为0.4，在甲醇中为0.52。然而，4-（N，N-二苯基氨基）苯乙烯取代的NIM-2和4-硝基苯乙烯取代的NIM-3在稀溶液中发光较弱，但在分子聚集条件下荧光效率高。NIM-2在固体状态下显示强的长波长发射和较大的斯托克斯位移。此外，NIM-3在混合溶液中因形成荧光有机纳米颗粒（FONs）而显示出意外的蓝绿色荧光。这两个例子归因于聚集诱导增强发射（AIEE）效应，这也合理地解释了细胞与NIM-2和NIM-3共育时观察到的明亮的细胞图像。此外，由于其在亚细胞水平上的行为，化合物NIM-2可用于识别癌细胞。
• Highly Selective and Sensitive Detection of Fe3+ by 1,8-Naphthalimide-Based Fluorescent Sensors
  作者：Shuping Wang、Dongmei Xu

  DOI：10.14233/ajchem.2013.14344

  日期：——

  Highly selective and sensitive detection of Fe3+ by two 1,8-naphthalimide-based fluorescent sensors, 2-(2-(dimethylamino)ethyl)-6-((2-(dimethylamino)ethyl)-amino)-1H-benzo[ de]isoquinoline-1,3(2H)-dione (MMN) and 2-(2-(diethylamino)ethyl)-6-((2-(diethylamino)-ethyl)amino)-1H-benzo[de]isoquinoline-1,3(2H)-dione (EEN) in N,N-dimethyl formamide is reported. The fluorescence intensity of MMN and EEN is greatly enhanced by Fe3+ ion with the response time of less than 1s. The maximum fluorescence intensity of the sensors is linearly dependent on the concentration of Fe3+ within the range of 10-100 μM. The binding stoichiometry indicates that a 2:1 complex is formed between Fe3+ and the sensor and the detection limits for MMN and EEN are 180 and 310 nM, respectively. A large number of biologically relevant ions show no obvious interferences with the detection.

  报道了通过两种基于1,8-萘酰亚胺的荧光传感器对Fe3+的高度选择性和敏感检测，分别为2-(2-(二甲氨基)乙基)-6-((2-(二甲氨基)乙基)氨基)-1H-苯并[de]异喹啉-1,3(2H)-二酮（MMN）和2-(2-(二乙氨基)乙基)-6-((2-(二乙氨基)乙基)氨基)-1H-苯并[de]异喹啉-1,3(2H)-二酮（EEN）在N,N-二甲基甲酰胺中的表现。MMN和EEN的荧光强度因Fe3+离子显著增强，响应时间不足1秒。传感器的最大荧光强度在线性范围内与Fe3+浓度（10-100 μM）成正比。结合化学计量表明Fe3+与传感器之间形成2:1的复合物，MMN和EEN的检测限分别为180和310 nM。大量生物相关离子对检测没有明显干扰。
• Water soluble 1,8-naphthalimide fluorescent pH probes and their application to bioimagings
  作者：Jian Xie、Yuhua Chen、Wen Yang、Dongmei Xu、Keda Zhang

  DOI：10.1016/j.jphotochem.2011.08.006

  日期：2011.9

  Two water soluble and high selective 1.8-naphthalimide fluorescent probes for protons have been synthesized by simple and efficient one-step reaction under very mild conditions. Their photophysical characteristics in Britton-Robinson buffer have been studied. All detections were carried out in aqueous media and a large number of biologically relevant ions showed no obvious interferences with the detection. Fluorescent imaging of living cells treated with the probe in different pH media indicated that the probe could provide extracelluar pH information by the cell's fluorescence. (C) 2011 Elsevier B.V. All rights reserved.
• Design, synthesis, and biological evaluation of new mitonafide derivatives as potential antitumor drugs
  作者：Ippolito Antonini、Rosaria Volpini、Diego Dal Ben、Catia Lambertucci、Gloria Cristalli

  DOI：10.1016/j.bmc.2008.08.027

  日期：2008.9

  A series of potential DNA-binding antitumor agents, 2-[omega-(alkylamino) alkyl]-6-[omega-(alkylamino) alkyl] amino}-1H-benzo[de] isoquinolin-1,3(2H)-diones and 1,7-bis6-[(omega-(dimethylamino) alkyl) amino]-1,3dioxo-1H-benzo[de] isoquinolin-2(3H)-yl}-4-methyl-4-azaheptanes, have been prepared as mitonafide derivatives. Their DNA-binding ability and cytotoxic activity have been evaluated. Some of the target compounds have shown high DNA affinity as well as relevant cytotoxic properties. (C) 2008 Elsevier Ltd. All rights reserved.
• A general strategy to quantify analytes through fluorescence chromaticity and luminosity
  作者：Tianyu Liang、Peiwei Yang、Tianhong Wu、Menghan Shi、Xiayu Xu、Taotao Qiang、Xiaolong Sun

  DOI：10.1016/j.cclet.2020.07.012

  日期：2020.11

  representative fluorescent probes, targeting pH, cysteine, hydrogen sulfide, hydrogen peroxide, palladium and hydrazine, were synthesized and tested. Without utilizing costly instrumentations, portable devices were employed to collect data of photographs from the fluorescence samples in responses to different analytes. Subsequently, the photographic images were digitally processed to generate calibration curves

  摘要利用荧光探针实现对分析物的定量分析，以实现一种快速，简便，精确的方法，是一个方便检测的目标，尤其是在原位。在本文中，我们报告了一种通常可用于通过荧光色度和发光度区分和定量分析物的方法。合成并测试了针对pH值，半胱氨酸，硫化氢，过氧化氢，钯和肼的七个代表性荧光探针。在不利用昂贵的仪器的情况下，采用便携式设备来响应不同的分析物而从荧光样品中收集照片数据。随后，在映射到CIE 1931 xyY标准色空间后，对照片图像进行数字处理以生成色度/发光度与浓度之间的校准曲线。良好的线性校准曲线和通过光谱技术对低误差的未知样品进行定量分析证明了该方法的可靠性。因此，我们展示了一种具有简单现场可构建/便携式设备的分析方法，有望在更多的荧光探针中应用