2-allyl-benzo[de]isoquinoline-1,3-dione | 39061-42-2

• 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-allyl-benzo[de]isoquinoline-1,3-dione
• 英文别名: N-(2-propenyl)-1,8-naphthalimide；N-allyl-1,8-naphthalimide；2-Prop-2-enylbenzo[de]isoquinoline-1,3-dione
• CAS: 39061-42-2
• 化学式: C₁₅H₁₁NO₂
• 分子量: 237.258
• InChiKey: SMFVXTGRZACURO-UHFFFAOYSA-N

物化性质

• 沸点：
  403.9±24.0 °C(Predicted)
• 密度：
  1.276±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  37.4
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-allyl-benzo[de]isoquinoline-1,3-dione 在 sodium tetrahydroborate 作用下， 以 乙醇 、 水 为溶剂， 反应 14.0h， 以79%的产率得到2-Allyl-2,3-dihydro-benzo[de]isoquinolin-1-one
  参考文献：
  名称：

  New and Convenient Synthesis of 2-Substituted 2,3-Dihydro-1H-benz[de]isoquinolin-1-ones

  摘要：

  通过在室温下使用钠或锌氢化硼对2-取代的1H-benz[de]isoquinoline-1,3(2H)-二酮进行化学选择性还原，获得了多种2-取代的2,3-二氢-1H-benz[de]isoquinolin-1-酮，产率很高。

  DOI：

  10.1246/bcsj.61.2238
• 作为产物：
  描述：

  苊 在 potassium dichromate 、 溶剂黄146 作用下， 以 乙醇 为溶剂， 反应 6.5h， 生成 2-allyl-benzo[de]isoquinoline-1,3-dione
  参考文献：
  名称：

  elinafide 修饰的双萘酰亚胺对 DNA 损伤和嵌入的抗癌活性

  摘要：

  Elinafide是一种双嵌萘酰亚胺，但由于副作用严重，已在II期临床试验中失败。鉴于此，我们对elinifide进行了修饰，通过在它们之间引入烷基链作为间隔基，合成了新型双萘酰亚胺。评估了这些衍生物在 10 µM 时对 60 种人类癌细胞系的抗癌活性。活性最强的化合物5e和9 h在五剂量浓度 (10 -4 –10 -8 M)下进一步评估。化合物5e (33.32 µM) 和9h (4.67 µM)均观察到低 MG-MID GI 50值。机制在体外探索通过紫外-可见、荧光和圆二色性等光谱技术进行 ct-DNA 结合研究。从获得的结果，观察到化合物5e与DNA的结合比9h更强。还进行了彗星试验以检查该化合物破坏癌细胞中 DNA 的能力。还检查了这些化合物对 HSA 的结合能力，结果表明化合物有效地结合 HSA，因此可以很容易地递送到靶位点。此外，还筛选了5a-i和9a-i对八种细菌菌株的抗菌

  DOI：

  10.1016/j.molliq.2023.121980

文献信息

• Surface modification of silica nanoparticles: a new strategy for the realization of self-organized fluorescence chemosensors
  作者：Enrico Rampazzo、Elena Brasola、Silvia Marcuz、Fabrizio Mancin、Paolo Tecilla、Umberto Tonellato

  DOI：10.1039/b502052b

  日期：——

  The self-organization of the proper subunits of a fluorescence chemosensor on the surface of silica nanoparticles allows the easy design and realization of new effective sensing systems. Commercially available silica particles (20 nm diameter) were functionalized with triethoxysilane derivatives of selective Cu(II) ligands and fluorescent dyes. Grafting of the sensor components to the particle surface ensures the spatial proximity between the sensor components and, as a consequence, binding of Cu(II) ions by the ligand subunits leads to quenching of the fluorescent units emission. In 9 : 1 DMSO–water solution, the coated silica nanoparticles (CSNs) selectively detect copper ions down to nanomolar concentrations. The operative range of the sensors can be tuned either by switching the ligand units or by modification of the components ratio. Sensors with the desired photophysical properties can be easily prepared by using different fluorescent dyes. Moreover, the organization of the network of sensor components gives rise to cooperative and collective effects: on one hand, the ligand subunits bound to the particle surfaces cooperate to form multivalent binding sites with an increased affinity for the Cu(II) ions; on the other hand, binding of a single metal ion leads to the quenching of several fluorescent groups producing a remarkable signal amplification.

  二氧化硅纳米颗粒表面上荧光化学传感器的适当亚基的自组装使得易于设计和实现新的有效传感系统。商业可获得的二氧化硅颗粒（20nm直径）通过三乙氧基硅烷衍生的选择性Cu(II)配体和荧光染料进行功能化。将传感器组件嫁接到颗粒表面上确保传感器组件之间的空间接近，因此，配体亚基结合Cu(II)离子导致荧光单元的荧光发射熄灭。在9：1 DMSO-水溶液中，涂层的二氧化硅纳米颗粒（CSNs）能够选择性地检测铜离子，检测极限达到纳摩尔浓度。传感器的操作范围可以通过切换配体单元或通过改变组件比例来进行调节。通过使用不同的荧光染料，可以很容易地制备具有所需光物理性质的传感器。此外，传感器组件的网络组织导致协同和集体效应：一方面，连接在颗粒表面上的配体亚基协作形成具有增加的亲和力的多价结合位点用于Cu(II)离子；另一方面，单个金属离子的结合导致几个荧光基团的熄灭，产生显著的信号增强。
• Preparation of pyrrolizinone derivatives <i>via</i> sequential transformations of cyclic allyl imides: synthesis of quinolactacide and marinamide
  作者：Milena Simic、Gordana Tasic、Predrag Jovanovic、Milos Petkovic、Vladimir Savic

  DOI：10.1039/c8ob00260f

  日期：——

  A facile synthetic route has been developed for the preparation of pyrrolizinone derivatives employing N-allyl imides as starting materials. The nucleophilic addition of a vinyl Grignard reagent/RCM/elimination sequence afforded pyrrolizinones in good yields and has been applied for the preparation of naturally occurring quinolactacide and marinamide.

  已经开发了一种以N-烯丙基酰亚胺为起始原料制备吡咯烷酮衍生物的简便合成途径。乙烯基格氏试剂/ RCM /消除序列的亲核加成以良好的收率提供了吡咯烷酮，并已用于制备天然存在的喹诺酸交酯和马来酰胺。
• GLYCOPROTEOMIC PROBES FOR FLUORESCENT IMAGING OF FUCOSYLATED GLYCANS IN VIVO
  申请人：Wong Chi-Huey

  公开号：US20110257376A1

  公开（公告）日：2011-10-20

  Methods are provided for labeling cellular glycans bearing azide groups via fluorescent labeling comprising Cu(I)-catalyzed [3+2] cycloaddition of a probe comprising alkynyl group. Generation of fluorescent probes from a nonfluorescent precursor, 4-ethynyl-N-ethyl-1,8-naphthalimide, by Cu(I)-catalyzed [3+2] cycloaddition of the alkyne group of the probe to an azido-modified sugar are provided. Incorporation of azido-containing fucose analog into glycoconjugates via the fucose salvage pathway are disclosed. Fluorescent visualization of fucosylated cells by flow cytometry of cells treated with 6-azidofucose labeled with click-activated fluorogenic probe or biotinylated alkyne is disclosed. Visualization of intracellular location of fucosylated glycoconjugates by fluorescence microscopy are disclosed.

  提供了一种通过荧光标记的方法来标记带有偶氮基团的细胞糖基，包括利用含炔基的探针进行铜(I)催化的[3+2]环加成。通过将非荧光前体4-乙炔基-N-乙基-1,8-萘酰亚胺经铜(I)催化的[3+2]环加成，将探针的炔基与偶氮修饰糖的偶氮基团结合生成荧光探针。通过富马醇拯救途径将含偶氮基的富马醇类似物纳入糖蛋白中。通过流式细胞术将经6-偶氮基富马醇标记的细胞与点击活化的荧光探针或生物素化炔烃处理，实现对富马基细胞的荧光可视化。通过荧光显微镜揭示富马基糖蛋白的胞内位置。
• ALKYNYL SUGAR ANALOGS FOR LABELING AND VISUALIZATION OF GLYCOCONJUGATES IN CELLS
  申请人：Sawa Masaaki

  公开号：US20120149887A1

  公开（公告）日：2012-06-14

  Methods for metabolic oligosaccharide engineering that incorporates derivatized alkyne-bearing sugar analogs as “tags” into cellular glycoconjugates are disclosed. Alkynyl derivatized Fuc and alkynyl derivatized ManNAc sugars are incorporated into cellular glycoconjugates. Chemical probes comprising an azide group and a visual or fluorogenic probe and used to label alkyne-derivatized sugar-tagged glycoconjugates are disclosed. Chemical probes bind covalently to the alkynyl group by Cu(I)-catalyzed [3+2] azide-alkyne cycloaddition and are visualized at the cell surface, intracellularly, or in a cellular extract. The labeled glycoconjugate is capable of detection by flow cytometry, SDS-PAGE, Western blot, ELISA, confocal microscopy, and mass spectrometry.

  揭示了将衍生的含炔基的糖类类似物作为“标签”纳入细胞糖结合物中的代谢寡糖工程方法。炔基衍生的Fuc和炔基衍生的ManNAc糖被纳入细胞糖结合物中。揭示了化学探针，包含一个偶氮基团和一个视觉或荧光探针，用于标记炔基衍生的糖标记的糖结合物。化学探针通过Cu(I)催化的[3+2]偶氮-炔基环加成与炔基团共价结合，并在细胞表面、细胞内或细胞提取物中被可视化。标记的糖结合物能够通过流式细胞仪、SDS-PAGE、Western blot、ELISA、共聚焦显微镜和质谱检测。
• Alkynyl sugar analogs for labeling and visualization of glycoconjugates in cells
  申请人：Academia Sinica

  公开号：US10317393B2

  公开（公告）日：2019-06-11

  Methods for metabolic oligosaccharide engineering that incorporates derivatized alkyne-bearing sugar analogs as “tags” into cellular glycoconjugates are disclosed. Alkynyl derivatized Fuc and alkynyl derivatized ManNAc sugars are incorporated into cellular glycoconjugates. Chemical probes comprising an azide group and a visual or fluorogenic probe and used to label alkyne-derivatized sugar-tagged glycoconjugates are disclosed. Chemical probes bind covalently to the alkynyl group by Cu(I)-catalyzed [3+2] azide-alkyne cycloaddition and are visualized at the cell surface, intracellularly, or in a cellular extract. The labeled glycoconjugate is capable of detection by flow cytometry, SDS-PAGE, Western blot, ELISA, confocal microscopy, and mass spectrometry.

  本发明公开了将衍生化的炔基糖类似物作为 "标签 "纳入细胞糖连接物的代谢寡糖工程方法。炔基衍生化的 Fuc 糖和炔基衍生化的 ManNAc 糖被加入到细胞糖连接物中。本发明公开了由叠氮基团和可视探针或荧光探针组成的化学探针，用于标记炔基衍生化糖标记的糖连接体。化学探针通过 Cu(I)-catalyzed [3+2] 叠氮-炔环化反应与炔基共价结合，并在细胞表面、细胞内或细胞提取物中可视化。标记的糖共轭物可通过流式细胞仪、SDS-PAGE、Western 印迹、ELISA、共聚焦显微镜和质谱仪进行检测。