2-(2-叠氮乙基)异吲哚-1,3-二酮 | 30250-66-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异吲哚及其衍生物
• 中文名称: 2-(2-叠氮乙基)异吲哚-1,3-二酮
• 英文名称: 2-(2-azidoethyl)isoindoline-1,3-dione
• 英文别名: N-(2-azidoethyl)phthalimide；2-(2-Azidoethyl)-1h-isoindole-1,3(2h)-dione；2-(2-azidoethyl)isoindole-1,3-dione
• CAS: 30250-66-9
• 化学式: C₁₀H₈N₄O₂
• mdl: MFCD14644895
• 分子量: 216.199
• InChiKey: WHYPSHDXYZFTHJ-UHFFFAOYSA-N

物化性质

• 熔点：
  58 °C

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  51.7
• 氢给体数：
  0
• 氢受体数：
  4

安全信息

• 海关编码：
  2929909090

反应信息

• 作为反应物：
  描述：

  2-(2-叠氮乙基)异吲哚-1,3-二酮 在 三苯基膦 、 水 作用下， 以 甲苯 为溶剂， 反应 1.0h， 生成 2-(2-氨基乙基)-1H-异吲哚-1,3(2H)-二酮
  参考文献：
  名称：

  EDTA and DTPA modified ligands as sequestering agents for uranyl decorporation

  摘要：

  Synthesis of modified EDTA and DTPA ligands and determination of their binding affinities for the uranyl cation are described.Thanks to a screening method, based on a chromophoric complex displacement procedure, chelating properties were studied in aqueous media under various pH conditions for evaluation of their in vivo uranyl-removal efficacy. Each ligand showed a more or less pronounced affinity for uranium. Specific ligands based on EDTA or DTPA analogues containing sulfocatecholamide (CAMS) were found to exhibit a significant affinity towards uranyl ion in acidic, neutral or basic conditions. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.11.065
• 作为产物：
  描述：

  N-羟乙基酞酰亚胺 在 四丁基碘化铵 sodium azide 、 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 5.0h， 以91%的产率得到2-(2-叠氮乙基)异吲哚-1,3-二酮
  参考文献：
  名称：

  A simple one-pot procedure for the direct conversion of alcohols into azides using TsIm

  摘要：

  A facile and efficient method for one-pot conversion of alcohols into azides using N-(p-toluenesulfonyl)imidazole (TsIm) is described. In this method, alcohols are refluxed with a mixture of NaN3, TsIm and triethylamine in the presence of catalytic amounts of tetra-n-butylammonium iodide (TBAI) in DMF affording the corresponding alkyl azides in good yields. This methodology is highly efficient for various structurally diverse alcohols with selectivity for ROH: 1 degrees > 2 degrees > 3 degrees. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2007.03.049

文献信息

• Iridium(III)-Catalyzed Selective Sulfonamidation of<i>o</i>-Carborane with Sulfonyl Azide by Carboxylic Acid-Assisted B(4)-H Bond Activation
  作者：Huanhuan Li、Fan Bai、Hong Yan、Changsheng Lu、Vladimir I. Bregadze

  DOI：10.1002/ejoc.201601537

  日期：2017.3.10

  An IrIII‐catalyzed direct cage B(4)–H bond sulfonamidation with carboxylic acid assistance is reported. This reaction proceeds in the absence of both external oxidants and ligands, and shows high yields and good functional group tolerance. In particular, direct cage B(4)–H bond amination was achieved by using aryl and aliphatic azides as nitrenoid sources for the first time.

  据报道，在羧酸的辅助下，Ir III催化的直接笼状B（4）-H键磺酰胺化反应。该反应在不存在外部氧化剂和配体的情况下进行，并且显示出高产率和良好的官能团耐受性。特别是，首次通过使用芳基和脂肪族叠氮化物作为类固醇源来实现直接笼状B（4）-H键胺化。
• Identification of highly potent and selective Cdc25 protein phosphatases inhibitors from miniaturization click-chemistry-based combinatorial libraries
  作者：Lanlan Jing、Gaochan Wu、Xia Hao、Fisayo A. Olotu、Dongwei Kang、Chin Ho Chen、Kuo-Hsiung Lee、Mahmoud E.S. Soliman、Xinyong Liu、Yuning Song、Peng Zhan

  DOI：10.1016/j.ejmech.2019.111696

  日期：2019.12

  chemistry synthesis via CuAAC reaction followed by in situ biological screening were used to discover selective Cdc25 inhibitors. The bioassay results showed that compound M2N12 proved to be the most potent Cdc25 inhibitor, which also act as a highly selective Cdc25C inhibitor and was about 9-fold potent than that of NSC 663284. Moreover, M2N12 showed remarkable anti-growth activity against the KB-VIN cell

  细胞分裂周期25（Cdc25）蛋白磷酸酶在细胞周期阶段之间的过渡中起着关键作用，其与各种癌症的关联已得到广泛证明，这使其成为抗癌治疗的理想靶标。尽管已经开发了几种Cdc25抑制剂，但大多数都显示出较低的活性和较差的亚型选择性。因此，发现对Cdc25亚型具有有效活性和显着选择性的新型小分子抑制剂非常重要，它不仅可以作为治疗癌症的药物，而且可以探索其在过渡过程中的作用机理。在这项研究中，通过CuAAC反应进行的微型平行点击化学合成，然后进行原位生物筛选，用于发现选择性的Cdc25抑制剂。生物测定结果表明，化合物M2N12被证明是最有效的Cdc25抑制剂，它也具有高选择性Cdc25C抑制剂的作用，其效力是NSC 663284的9倍。此外，M2N12对KB表现出显着的抗生长活性。 -VIN细胞系，与PXL和NSC 663284等效。采用全原子分子动力学（MD）模拟方法来探究M2N12对Cdc25C
• Conversion of leucomycin-A3 antibiotic into novel triazole analogues via regio- and diastereoselective SN1′ substitution with allylic rearrangement and 1,3-dipolar cycloaddition of CuAAC type
  作者：Joanna Domagalska、Krystian Pyta、Piotr Przybylski

  DOI：10.1016/j.tetlet.2016.02.113

  日期：2016.4

  nucleophilic substitution of josamycin’s dienol system in the aglycone yielded novel products having an alkyne group attached at the C(13) carbon atom. Detailed 1H–1H NOESY and 1H–13C HMBC investigations together with DFT calculations indicated the C(13S) configuration within the structures of alkyne-functionalized leucomycins. Analysis of the relationship between the rate of nucleophilic substitution and concentration

  考虑到交联霉素（leucomycin-A 3）缩醛官能团的化学反应复杂，醛缩醛的醛化反应继而亲核取代交联糖苷配基中的乙醛，产生了在C（13）碳原子上连接有炔基的新产物。详细的1 H– 1 H NOESY和1 H– 13 C HMBC研究以及DFT计算表明C（13 S）在炔烃官能化的白霉素的结构内进行配置。对亲核取代速率与浓度之间关系的分析揭示了取代的单分子机理，其中离去基团的质子化是速率确定步骤。使用CuAAC反应进一步将糖苷配基上的炔烃取代基转化为可得到带有取代的1,2,3-三唑环的新型杂环白霉素类似物。
• 16-Membered Macrolide Lactone Derivatives Bearing a Triazole-Functionalized Arm at the Aglycone C13 Position as Antibacterial and Anticancer Agents
  作者：Joanna Domagalska、Anna Janas、Krystian Pyta、Paulina Pecyna、Piotr Ruszkowski、Lech Celewicz、Marzena Gajecka、Franz Bartl、Piotr Przybylski

  DOI：10.1002/cmdc.201600250

  日期：2016.9.6

  indexes [SI; calculated relative to the human dermal fibroblast (HDF) cell line], even higher than that of the reference compound cytarabine. Results of molecular docking studies of this type of macrolide antibiotics at the ribosomal tunnel, together with experimentally determined lipophilicity and aqueous solubility values, as well as biological assay data revealed the importance of the introduced functional

  合成了一系列具有减少的醛基的新的C13-三唑桥连和C13-醚白细胞生成素类似物。具有最高抗菌[MIC值（表皮葡萄球菌，肺炎链球菌）的衍生物：约2-4杯mL-1；[2.55-5.09微米]和细胞毒性[IC50值（HeLa，KB，MCF-7，A549，HepG2细胞）：约1.35-3.70微米]效力是具有最佳水溶性的，并且在C13位置带有糖基三唑臂糖苷配基。这些衍生物优先结合在核糖体通道上，并显示出最具吸引力的选择性指数[SI; 相对于人皮肤成纤维细胞（HDF）细胞系] [计算]，甚至高于参考化合物阿糖胞苷。这类大环内酯类抗生素在核糖体隧道分子对接研究的结果，结合实验确定的亲脂性和水溶性值以及生物学测定数据，揭示了在糖苷配基C13臂上引入的官能团对未来抗癌和抗菌药物候选产品的重要性。我们的结果清楚地表明，这些类型的大环内酯类药物的高抗菌和抗癌活性不一定取决于糖苷内酯环上醛基的存在。
• Sequential One-Pot Ruthenium-Catalyzed Azide−Alkyne Cycloaddition from Primary Alkyl Halides and Sodium Azide
  作者：Johan R. Johansson、Per Lincoln、Bengt Nordén、Nina Kann

  DOI：10.1021/jo200134a

  日期：2011.4.1

  simple sequential one-pot RuAAC reaction, affording 1,5-disubstituted 1H-1,2,3-triazoles in good to excellent yields starting from an alkyl halide, sodium azide, and an alkyne, is reported. The organic azide is formed in situ by treating the primary alkyl halide with sodium azide in DMA under microwave heating. Subsequent addition of [RuClCp*(PPh3)2] and the alkyne yielded the desired cycloaddition product

  据报道，从烷基卤化物，叠氮化钠和炔烃开始，实验上简单的连续一锅RuAAC反应以良好或优异的产率提供了1,5-二取代的1 H -1,2,3-三唑。通过在微波加热下在DMA中用叠氮化钠处理伯烷基卤化物来原位形成有机叠氮化物。在进一步的微波辐射之后，随后加入[RuClCp *（PPh 3）2 ]和炔烃，得到所需的环加成产物。