6-bromo-2-cetyl-1H-benzo[de]isoquinoline-1,3-(2H)-dione | 1087053-43-7

• 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: 6-bromo-2-cetyl-1H-benzo[de]isoquinoline-1,3-(2H)-dione
• 英文别名: 4-bromo-N-hexadecylnaphthalene-1,8-dicarboximide；4-bromo-N-cetanylnaphthalimide；N-hexadecyl-4-bromo-1,8-naphthalimide；6-bromo-2-hexadecylbenzo[de]isoquinoline-1,3-dione
• CAS: 1087053-43-7
• 化学式: C₂₈H₃₈BrNO₂
• 分子量: 500.519
• InChiKey: FYDQQVSQGJFMFJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.68
• 重原子数：
  32.0
• 可旋转键数：
  15.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  37.38
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  6-bromo-2-cetyl-1H-benzo[de]isoquinoline-1,3-(2H)-dione 在 四丁基溴化铵 、 三苯基膦 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 二氯甲烷 、 乙二醇甲醚 为溶剂， 生成 6-((2-bromoethyl)amino)-2-cetyl-1H-benzo[de]isoquinoline-1,3-(2H)-dione
  参考文献：
  名称：

  Naphthalimides exhibit in vitro antiproliferative and antiangiogenic activities by inhibiting both topoisomerase II (topo II) and receptor tyrosine kinases (RTKs)

  摘要：

  Novel naphthalimide derivatives were designed and synthesized to modulate both topoisomerase II (topo II) and receptor tyrosine kinases (RTKs). Most target compounds exhibited effective and selective antiproliferative activities against three cancer cell lines by inhibiting topo II. The IC50 values ranged from 1.5 to 19.1 mu M. Moreover, compounds 8d and 12d moderately inhibited various angiogenesis-related RTKs, including FGFR1, VEGFR2 and PDGFR alpha. The representative compound 8d was then proved to possess antiangiogenic activity, which was evidenced by the inhibition of migration and tube formation activities of HMEC-1 cells. To our knowledge, it is the first time naphthalimides were identified as tyrosine kinases inhibitors (TKIs) besides their conventional cytotoxicity. (C) 2013 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.05.002
• 作为产物：
  描述：

  十六胺 、 4-溴-1,8-萘二甲酸酐 在 溶剂黄146 作用下， 反应 4.0h， 以93%的产率得到6-bromo-2-cetyl-1H-benzo[de]isoquinoline-1,3-(2H)-dione
  参考文献：
  名称：

  Hyperbranched polyyne containing naphthalimide moiety as a fluorescent chemosensor for mercury ion

  摘要：

  开发作为荧光传感器的多嵌段共轭聚合物对检测痕量有毒离子极具吸引力。本文设计并合成了一种以聚三(4-乙炔基苯基)胺（PTEPA）为核心，以苯甲酰硫脲-萘二甲酰亚胺（NAP）为汞（II）检测单元的新型超支化聚乙烯。在四氢呋喃条件下，加入 Hg (II) 离子会将化学计量器的硫脲单元转化为咪唑啉分子，而咪唑啉分子是一个电子负载较少的基团，因此会减少荧光体内部的电子析出。发射最大值出现蓝移，荧光强度增加。为了证实传感器对汞离子的选择性，还用其他二价金属离子对其进行了滴定。在荧光光谱中没有观察到明显的变化。

  DOI：

  10.1007/s11458-010-0102-z

文献信息

• Introduction of methyl groups on vinylene segments of phenylene vinylene systems: synthesis and properties
  作者：Khai Leok Chan、Alan Sellinger

  DOI：10.1039/b909500d

  日期：——

  A facile synthetic route towards phenylene vinylene systems with methyl substituents at the vinyl linkages is demonstrated through palladium catalyzed Heck coupling of 1,4-diisopropenylbenzene with aryl bromides. The coupling leads to a series of model compounds that feature, in some cases, direct access to a trans-configuration at the double bonds. The oxidative stability of these systems is surprisingly unaffected by the presence of allylic C-H bonds in the methyl substituents. The methyl substituents modulate the electronic properties of the phenylene vinylene systems by inducing a significant twist to the conjugated backbone. The study suggests that the introduction of methyl groups at vinylene sites is a viable alternative to functionalising and tuning the properties of phenylene vinylene systems.

  通过钯催化的Heck耦合反应，将1,4-二异丙烯基苯与芳基溴化物反应，展示了一条制备含有乙烯链上甲基取代基的苯并乙烯系统的简便合成路线。这种耦合反应产生了一系列模型化合物，在某些情况下，可以直接获得双键的反式构型。这些系统的氧化稳定性意外地不受甲基取代基中烯丙基C-H键的影响。甲基取代基通过在共轭骨架上引入显著扭曲，调节了苯并乙烯系统的电子性质。研究表明，在乙烯链位置引入甲基是一种有效的替代方法，用于功能化和调节苯并乙烯系统的性质。
• Long alkyl side-chains impede exciton interaction in organic light harvesting crystals
  作者：Kalaivanan Nagarajan、Gopika Gopan、Rijo T. Cheriya、Mahesh Hariharan

  DOI：10.1039/c7cc02322g

  日期：——

  Side-chains at the imidic position of naphthalimide rendered a firm control over (i) the degrees of π–π overlap and (ii) distances between the perylenimide units in a crystalline naphthalimide–perylenimide dyad as determined using single crystal XRD and Hirshfeld surface analyses. Steady-state and time-resolved electronic spectroscopy in addition to DFT calculations revealed a decline in intermolecular

  使用单晶XRD和Hirshfeld表面分析确定，在萘二甲酰亚胺类似位置上的侧链对（i）π-π重叠程度和（ii）萘二甲酰亚胺-邻苯二甲酰亚胺二元结晶中的邻苯二甲酰亚胺单元之间的距离提供了牢固的控制。 。稳态和时间分辨电子光谱以及DFT计算表明，由于烷基链的干扰，分子间的激子相互作用下降。
• [EN] ? (PI)-CONJUGATED FLUOROIONOPHORES AND METHOD FOR DETERMINING AN ALKALI ION<br/>[FR] FLUOROIONOPHORES p-CONJUGUÉS ET MÉTHODE DE DOSAGE D'UN ION ALCALIN
  申请人：UNIV POTSDAM

  公开号：WO2012120141A1

  公开（公告）日：2012-09-13

  The present invention relates to π-conjugated fluoroionophores, methods for their preparation, and their use and a method for determining an alkali ion. Fluoroionophoric compounds of the general formula I are described Ionophore – π-Linker - Fluorophore (I) wherein the Ionophore is an anilino containing crown ether or cryptand with one or more anilino donor moieties as electron donors, forming a stable complex with an alkali metal ion the π-Linker is an aromatic or heteroaromatic conjugative linking moiety, and the Fluorophore is an electron acceptor moiety. Variation of the ionophoric unit offers a broad spectrum of detectable K+ and Na+ -concentrations, ranging from high concentration around 800 mM down to very low concentrations around 3 mM. The fluoroionophores have great potential for application in fluorescent optode system based blood analyzing equipment for methods and kits for the determination of K+ and Na+ concentrations in biological systems, either in vitro or in vivo, using embodiments of the disclosed fluoroionophores.

  本发明涉及π-共轭氟离子探针，其制备方法以及它们的使用和一种用于确定碱金属离子的方法。描述了一般式I的氟离子探针化合物 离子载体 - π-连接体 - 荧光团（I），其中离子载体是含有一个或多个苯胺供体基团作为电子给体的冠醚或cryptand，与碱金属离子形成稳定络合物，π-连接体是芳香或杂芳共轭连接基团，荧光团是电子受体基团。离子载体单元的变化提供了广泛的可检测K+和Na+浓度范围，从约800 mM的高浓度到约3 mM的非常低浓度。这些氟离子探针在基于荧光光电系统的血液分析设备中具有巨大的应用潜力，用于检测生物系统中K+和Na+浓度的方法和试剂盒，无论是体外还是体内，都可以使用所披露的氟离子探针的实施方式。
• A pH sensitive ratiometric fluorophore and its application for monitoring the intracellular and extracellular pHs simultaneously
  作者：Jin Zhou、Canliang Fang、Tianjun Chang、Xiangjun Liu、Dihua Shangguan

  DOI：10.1039/c2tb00179a

  日期：——

  Intracellular and extracellular pH plays a key role in many cell biological processes. Probes for simultaneously monitoring the pH change inside and outside living cells are rarely available. In this paper, we describe a new ratiometric pH fluorophore that was synthesized by condensation of 4-bromine-1,8-naphthalimides and 3-amino-1,2,4-triazole. In the range of pH 5–8, the only N–H in the heterocycle-fused aromatic ring system of this fluorophore undergoes a reversible deprotonation–protonation process, which results in a large red shift of the absorption and emission spectra. In aqueous solution, this fluorophore exhibits good pH selectivity, high photostability, high tolerance to ionic strength, and high fluorescence quantum yield in both the acid and base forms. A long chain derivative of this fluorophore (HNNA) was designed for cellular pH sensing. HNNA was found to locate on the membrane structure of the cells, and was successfully used for mapping the pH change in both the extracellular microenvironment and the inner cells by confocal imaging.

  细胞内外的 pH 值在许多细胞生物过程中发挥着关键作用。目前很少有探针能同时监测活细胞内外的 pH 值变化。在本文中，我们介绍了一种新的 pH 计比率荧光团，它是由 4-溴-1,8-萘二甲酰亚胺和 3-氨基-1,2,4-三唑缩合合成的。在 pH 值为 5-8 的范围内，这种荧光团的杂环融合芳环系统中唯一的 N-H 发生可逆的去质子化-质子化过程，从而导致吸收和发射光谱发生较大的红移。在水溶液中，这种荧光团具有良好的 pH 选择性、高光稳定性、对离子强度的高耐受性，并且在酸性和碱性形式下都具有高荧光量子产率。这种荧光团的长链衍生物（HNNA）被设计用于细胞 pH 值传感。研究发现，HNNA 可定位在细胞膜结构上，并通过共聚焦成像技术成功绘制了细胞外微环境和细胞内 pH 值变化图。
• Synthesis of 4-aziridino[C60]fullerene-1,8-naphthalimide (C60-NI dyads) and their photophysical properties
  作者：Fengrui Liu、Weiqiong Du、Qin Liang、Yuqin Wang、Jianmin Zhang、Jingwei Zhao、Shizheng Zhu

  DOI：10.1016/j.tet.2010.05.019

  日期：2010.7

  A series of 4-aziridino[C-60]fullerene-1,8-naphthalimide (C-60-NI) dyads 4 ([6,6]-closed ring) were synthesized as the only addition product from the reaction of C-60 with the corresponding azide compounds 3 under microwave irradiation in good yield. A quenching of fluorescence was shown in dyads 4, and this decay was evidenced to be an intramolecular process. (C) 2010 Elsevier Ltd. All rights reserved.