3,6-dinitro-1,8-naphthalic anhydride | 3807-80-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 3,6-dinitro-1,8-naphthalic anhydride
• 英文别名: 5,8-Dinitro-1H,3H-benzo[de]isochromene-1,3-dione；7,11-dinitro-3-oxatricyclo[7.3.1.05,13]trideca-1(12),5(13),6,8,10-pentaene-2,4-dione
• CAS: 3807-80-5
• 化学式: C₁₂H₄N₂O₇
• mdl: MFCD00227027
• 分子量: 288.173
• InChiKey: LHFDXTKVBLMYJH-UHFFFAOYSA-N

物化性质

• 熔点：
  213-217°C (dec.)
• 沸点：
  587.0±40.0 °C(Predicted)
• 密度：
  1.796±0.06 g/cm3(Predicted)
• 溶解度：
  丙酮（微溶），乙酸乙酯（微溶）

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  21
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  135
• 氢给体数：
  0
• 氢受体数：
  7

安全信息

• 海关编码：
  2932999099

反应信息

• 作为反应物：
  描述：

  3,6-dinitro-1,8-naphthalic anhydride 在 palladium 10% on activated carbon 、 甲酸铵 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 以89%的产率得到3,6-diamino-1,8-naphthalic anhydride
  参考文献：
  名称：

  Design, synthesis, biophysical and biological studies of trisubstituted naphthalimides as G-quadruplex ligands

  摘要：

  A series of trisubstituted naphthalimides have been synthesized and evaluated as telomeric G-quadruplex ligands by biophysical methods. Affinity for telomeric G-quadruplex AGGG(TTAGGG)(3) binding was first screened by fluorescence titrations. Subsequently, the interaction of the telomeric G-quadruplex with compounds showing the best affinity has been studied by isothermal titration calorimetry and UV-melting experiments. The two best compounds of the series tightly bind the telomeric quadruplex with a 2:1 drug/DNA stoichiometry. These derivatives have been further evaluated for their ability to inhibit telomerase by a TRAP assay and their pharmacological properties by treating melanoma (M14) and human lung cancer (A549) cell lines with increasing drug concentrations. A dose-dependent inhibition of cell proliferation was observed for all cellular lines during short-term treatment. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.08.062
• 作为产物：
  描述：

  3-硝基-1,8-萘二甲酸酐 在 硫酸 、 硝酸 作用下， 反应 1.5h， 生成 3,6-dinitro-1,8-naphthalic anhydride
  参考文献：
  名称：

  通过基于结构的虚拟筛选和新颖的AlphaScreen分析鉴定作为新型Atg4B抑制剂的苯并[ cd ]吲哚-2（1 H）-一。

  摘要：

  靶向自噬是一种有前途的癌症治疗策略。结果，新型自噬抑制剂的鉴定是一个新兴的研究领域。在本文中，我们报告了结合基于MS的检测和基于结构的高通量虚拟筛选的新型AlphaScreen HTS检测的开发，该检测已将苯并[ cd ] indol-2（1 H）-作为一种靶向Atg4B的新型支架。因此，最初的筛选活动导致鉴定了带有氯醇部分的NSC126353和NSC611216。初始命中的结构-活性关系分析提供了带有7-氨基苯并[ cd]的优化铅化合物33] indol-2- [ 1H ]-一个支架和一个丙基取代氯。还通过测量LC3-II和p62蛋白水平来研究细胞中自噬的抑制作用。此外，33与奥沙利铂联合的协同作用导致人结肠直肠腺癌细胞系HT-29的细胞死亡增加。我们相信，开发的基于AlphaScreen和MS的检测方法可以成为实现高通量鉴定新型Atg4B抑制剂的关键工具。而且，氨基苯并[ cd ]吲哚-2-

  DOI：

  10.1016/j.ejmech.2019.05.086

文献信息

• Isoquinolones
  申请人：Warner-Lambert Company

  公开号：US06177423B1

  公开（公告）日：2001-01-23

  Benzo[de]isoquinoline-1,3-dione of Formula or a pharmaceutically acceptable salt thereof wherein R is hydrogen or a protecting group typically used in the art for protecting alcohols and R1-R5 are each independently chosen from H, Cl, Br, F, straight or branched alkyl C1-C8 alkyl, C3-C8 cycloalkyl, heterocycle or bridged heterocycle of 4-9 atoms containing 1-3 heteroatoms, —(CR′2)nOR6, —(CR′2)nN(R6)2, —(CR′2)nNR6COR7, —(CR′2)nNR6SO2OR7, —(CR′2)nNR6SO2 N(R6)2, —(CR′2)nOSO2 N(R6)2, —(CR′2)nCN, —(CR′2)n(NOR6)R7, NO2, CF3, —(CR′2)nSOmR7, —(CR′2)nSOmR7, —(CR′2)nCO2R6, —(CR′2)nCON(R6)2, Ph, and any two of R1-R5 may form a substituted or unsubstituted ring of 5-7 total atoms having 0-2 heteroatoms are claimed which are selective inhibitors of bacterial DNA gyrase and DNA topoisomerase useful in antibacterial agents. Methods for their preparation and formulation as well as novel intermediates useful in the preparation of the final products are also claimed.

  苯并[de]异喹啉-1,3-二酮的化学式，或其在药学上可接受的盐，其中R为氢或通常用于保护醇的艺术中的保护基，R1-R5分别独立地选择自H、Cl、Br、F、直链或支链烷基C1-C8烷基、C3-C8环烷基、杂环或含有1-3个杂原子的4-9个原子的桥接杂环，—(CR′2)nOR6、—(CR′2)nN(R6)2、—(CR′2)nNR6COR7、—(CR′2)nNR6SO2OR7、—(CR′2)nNR6SO2 N(R6)2、—(CR′2)nOSO2 N(R6)2、—(CR′2)nCN、—(CR′2)n(NOR6)R7、NO2、CF3、—(CR′2)nSOmR7、—(CR′2)nSOmR7、—(CR′2)nCO2R6、—(CR′2)nCON(R6)2、Ph，以及R1-R5中的任意两个可形成具有0-2个杂原子的5-7个总原子的取代或未取代环的选择性细菌DNA旋转酶和DNA拓扑异构酶抑制剂，适用于抗菌剂。还声明了它们的制备和配方方法，以及在制备最终产品中有用的新型中间体。
• Synthesis and Characterization of Dimaleimide Fluorogens Designed for Specific Labeling of Proteins
  作者：Stéphane Girouard、Marie-Hélène Houle、Alain Grandbois、Jeffrey W. Keillor、Stephen W. Michnick

  DOI：10.1021/ja045742x

  日期：2005.1.1

  spectral characterization studies. In this way, the title compounds serve as fluorogens capable of detection of small thiols or appropriately sized dithiols. Recombinant alpha-helical proteins were then designed to bear two cysteine residues capable of regioselective dithiol addition reaction with the dimaleimide fluorogens, thus acting as spatially encoded substrates that form specifically labeled covalent

  制备了一系列带有两个直接连接到荧光核的马来酰亚胺基团的芳香族化合物。所得衍生物在马来酰亚胺基团进行其典型的硫醇加成反应之前不会发出荧光，从而消除了它们淬灭荧光的能力，如动力学和光谱表征研究所示。以此方式，标题化合物用作能够检测小硫醇或适当大小的二硫醇的荧光剂。然后将重组 α 螺旋蛋白设计为带有两个半胱氨酸残基，能够与二马来酰亚胺荧光团进行区域选择性二硫醇加成反应，从而充当形成特定标记共价复合物的空间编码底物。
• N-(Aminoalkyl)imide antineoplastic agents. Synthesis and biological activity
  作者：Robert K. Y. Zee-Cheng、C. C. Cheng

  DOI：10.1021/jm00147a016

  日期：1985.9

  substitution on certain chosen ring systems, and (d) combinations of the aforementioned variants. Preliminary biological activity screening indicated that N-(dialkylaminoethyl)imides of the 3,6-dinitro- and 3,6-diamino-1,8-naphthalic acid system possessed prominent antileukemia and antimelanoma activity in both in vitro and in vivo experimental tumor systems.

  我们在1978年发现的1,4-二羟基-5,8-双[[[[[[[2-[（（2-羟乙基）氨基]乙基]氨基]蒽醌（DHAQ）的侧链特征与那些相似最近由其他研究者发现的3-硝基-1,8-萘甲酸N-取代的酰亚胺的研究，使我们对各种酰亚胺的N-（氨基烷基）取代的衍生物进行了系统的研究。研究领域包括：（a）环系统的选择，（b）侧链的修饰，（c）在某些选定的环系统上的取代，以及（d）上述变体的组合。初步生物学活性筛选表明，在体内和体外实验肿瘤系统中，3,6-二硝基-和3,6-二氨基-1,8-萘系的N-（二烷基氨基乙基）酰亚胺具有显着的抗白血病和嗜黑素瘤活性。 。
• Fluorescent labeling of specific protein targets in vitro and in vivo
  申请人：Keillor W. Jeffrey

  公开号：US20060147948A1

  公开（公告）日：2006-07-06

  New methods are provided for the post-genomic era that will permit the analysis of the dynamic expression and localization of gene products in living cells. Herein we propose the development of such a method from a bioorganic approach involving organic synthesis and protein engineering. Specifically, novel compounds bearing two maleimide groups attached directly to fluorescent cores will be prepared, whose latent fluorescence is quenched until their maleimide groups undergo a specific thiol addition reaction. Complementary a-helical proteins are designed bearing two cysteine residues appropriately positioned to react with our novel fluorogens. Genetically fusing our helical probe peptides to test proteins of interest, we can selectively label the target sequence in living cells with our small synthetic fluorogenic molecules. The scope of this technique is described in the context of studying protein localization and protein-protein interactions in living cells.

  提供了新的方法用于后基因组时代，这些方法将允许分析基因产物在活细胞中的动态表达和定位。在这里，我们提出了从生物有机化学方法出发的一种方法的发展，涉及有机合成和蛋白工程。具体来说，将制备带有两个马来酰亚胺基团直接连接到荧光核心的新化合物，其潜在荧光在其马来酰亚胺基团经历特定巯基加成反应之前被熄灭。设计了具有两个半胱氨酸残基的互补α-螺旋蛋白，这些残基被适当地定位以与我们的新型荧光基团发生反应。通过遗传融合我们的螺旋探针肽到感兴趣的蛋白质上，我们可以使用我们的小型合成荧光基团在活细胞中选择性地标记目标序列。在研究蛋白质在活细胞中的定位和蛋白质相互作用方面描述了这种技术的范围。
• [EN] SMALL MOLECULE MODIFIERS OF MICRORNA MIR-122<br/>[FR] MODIFICATEURS À PETITE MOLÉCULE DE MICROARN MIR-122
  申请人：UNIV NORTH CAROLINA STATE

  公开号：WO2011091209A1

  公开（公告）日：2011-07-28

  MicroRNAs are a class of endogenous regulators of gene function. Aberrant regulation of microRNAs has been linked to various human diseases, most importantly cancer. Small molecule intervention of microRNA misregulation has the potential to provide new therapeutic approaches to such diseases. microRNA miR-122 is the most abundant microRNA in the liver and is involved in hepatocellular carcinoma development and hepatitis C virus (HCV) infection. Small molecule inhibitors and activators of the microRNA miR-122 are described, and methods for their identification are reported. These small molecule inhibitors reduce viral replication in liver cells and thus represent a new approach to the treatment of HCV infections. Moreover, small molecule activation of miR-122 in liver cancer cells selectively induced apoptosis through caspase activation, and thus has implications in cancer chemotherapy.

  微小RNA是一类内源性基因功能调节因子。微小RNA的异常调节与各种人类疾病有关，尤其是癌症。对微小RNA的小分子干预可能为这些疾病提供新的治疗途径。微小RNA miR-122是肝脏中最丰富的微小RNA，参与了肝细胞癌和丙型肝炎病毒（HCV）感染的发展。描述了微小RNA miR-122的小分子抑制剂和激活剂，并报告了其鉴定方法。这些小分子抑制剂可以减少肝细胞中的病毒复制，因此代表了治疗HCV感染的新方法。此外，在肝癌细胞中通过小分子激活miR-122可选择性诱导凋亡，通过激活半胱氨酸蛋白酶而在癌症化疗中具有重要意义。

表征谱图