2-羟基亚氨基-N-(4-硝基苯基)-乙酰胺 | 17122-62-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 2-羟基亚氨基-N-(4-硝基苯基)-乙酰胺
• 英文名称: N-(α-Oximino-acetyl)-4-nitro-anilin
• 英文别名: hydroxyimino-acetic acid-(4-nitro-anilide)；Hydroxyimino-essigsaeure-(4-nitro-anilid)；Oximinoessigsaeure-(4-nitro-anilid)；2-(Hydroxyimino)-N-(4-nitrophenyl)acetamide；2-hydroxyimino-N-(4-nitrophenyl)acetamide
• CAS: 17122-62-2
• 化学式: C₈H₇N₃O₄
• mdl: MFCD00748380
• 分子量: 209.161
• InChiKey: LULLDSAESQNSDI-UHFFFAOYSA-N

物化性质

• 熔点：
  204-206 °C
• 密度：
  1.47±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  108
• 氢给体数：
  2
• 氢受体数：
  5

安全信息

• 海关编码：
  2928000090

反应信息

• 作为反应物：
  描述：

  2-羟基亚氨基-N-(4-硝基苯基)-乙酰胺 在 硫酸 、 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 生成 5-Nitro-2,3-dioxo-2,3-dihydro-indole-1-carboxylic acid methylamide
  参考文献：
  名称：

  Biological activities and quantitative structure-activity relationships of spiro[imidazolidine-4,4'(1'H)-quinazoline]-2,2',5(3'H)-triones as aldose reductase inhibitors

  摘要：

  A series of spiro[imidazolidine-4,4'(1'H)-quinazoline]-2,2',5(3'H)-triones were prepared and tested for aldose reductase inhibitory activity. The 6'-halogenated derivatives were found to be highly potent in vitro inhibitors of male rabbit lens aldose reductase and in vivo inhibitors of polyol accumulation in the sciatic nerves of galactosemic rats. Of these, (4R)-6'-chloro-3'-methylspiro[imidazolidine-4,4'(1'H)-quinazoline]-2,2',5(3'H)-trione (67) showed the most potent in vitro and in vivo activities. An oral dose of 3 g/kg of compound 67 caused neither death nor behavioral abnormality in the preliminary acute toxicity study using mice and rats. Compound 67 was selected as a candidate for further evaluation. The quantitative structure-activity relationships in this series are also discussed.

  DOI：

  10.1021/jm00089a021
• 作为产物：
  描述：

  在 盐酸羟胺 作用下， 以 乙醇 、 水 为溶剂， 反应 2.0h， 生成 2-羟基亚氨基-N-(4-硝基苯基)-乙酰胺
  参考文献：
  名称：

  An improved synthesis of isonitrosoacetanilides

  摘要：

  A novel two-step synthesis of isonitrosoacetanilides [2-(hydroxyimino)-N-phenylacetamides] has been developed, involving the initial acylation of aniline derivatives with 2,2-diacetoxyacetyl chloride, followed by reaction with hydroxylamine hydrochloride. The method works equally well with a variety of different aniline derivatives, including those with poor aqueous solubility and those containing electron rich ortho-substituents, neither of which react well under traditional conditions. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2005.10.046

文献信息

• Synthesis, modification and docking studies of 5-sulfonyl isatin derivatives as SARS-CoV 3C-like protease inhibitors
  作者：Wei Liu、He-Min Zhu、Guo-Jun Niu、En-Zhi Shi、Jie Chen、Bo Sun、Wei-Qiang Chen、Hong-Gang Zhou、Cheng Yang

  DOI：10.1016/j.bmc.2013.11.028

  日期：2014.1

  possible SARS-CoV 3CLpro inhibitors was designed, synthesized, and evaluated by in vitro protease assay using fluorogenic substrate peptide, in which several showed potent inhibition against the 3CLpro. Structure–activity relationship was analyzed, and possible binding interaction modes were proposed by molecular docking studies. Among all compounds, 8k1 showed most potent inhibitory activity against

  严重急性呼吸系统综合症 (SARS) 是由 SARS-CoV 引起的严重危及生命且致命的呼吸道疾病。SARS-CoV 含有与主要小核糖核酸病毒蛋白酶 3CL pro类似的胰凝乳蛋白酶样主要蛋白酶。3CL pro在病毒复制周期中起着关键作用，是 SARS 抑制剂开发的潜在目标。设计、合成了一系列靛红衍生物作为可能的 SARS-CoV 3CL pro抑制剂，并通过使用荧光底物肽的体外蛋白酶测定进行评估，其中几种对 3CL pro显示出有效的抑制作用. 分析了构效关系，并通过分子对接研究提出了可能的结合相互作用模式。在所有化合物中，8k 1对 3CL pro显示出最有效的抑制活性(IC 50  = 1.04 μM)。这些结果表明，这些抑制剂有可能被开发成抗 SARS 药物。
• A novel strategy to the synthesis of 4-anilinoquinazoline derivatives
  作者：Zheng Wang、Cuiling Wang、Yanni Sun、Ning Zhang、Zhulan Liu、Jianli Liu

  DOI：10.1016/j.tet.2013.12.028

  日期：2014.1

  A novel approach to prepare 4-anilinoquinazoline derivatives based on the transformation of indoline-2,3-dione to formamidine was developed. The processes with this approach are simple, efficient, and environmentally friendly. The efficiency of this approach was evaluated by synthesizing 17 4-anilinoquinazolines and comparing the obtained yields with those achievable through conventional synthetic

  开发了一种基于吲哚啉-2,3-二酮向甲am的转化制备4-苯胺基喹唑啉衍生物的新方法。使用这种方法的过程简单，高效且对环境友好。通过合成17种4-苯胺基喹唑啉并将获得的收率与通过常规合成方法可获得的收率进行比较，评估了该方法的效率。这是第一次合成化合物8d，8e，8h和13b - f。观察到这些化合物的IR和UV光谱的特征以及它们的取代基对光谱的影响。
• Synthesis of Novel Triazol Compounds containing Isatin as Potential Antibacterial and Antifungal Agents by Microwave and Conventional Methods
  作者：Musa Özil、Emre Menteşe、Fatih Yilmaz、Fatih İslamoğlu、Bahittin Kahveci

  DOI：10.3184/174751911x13043524455143

  日期：2011.5

  Microwave irradiation has been used to accelerate the conversion of isatin (1a) and 5-nitroisatin (1b) into their Schiff bases 3-[5’-aryl(alkyl)-2’,4’-dihydro-1’,2’,4’-triazol-3’-on-4’-yl]iminoisatin (3a–g) and 3-[5’-aryl(alkyl)-2’,4’-dihydro-1’,2’,4’-triazol-3’-on-4’-yl]imino-5-nitroisatin (4a–g), respectively. Reaction was achieved by microwave-induced technique, which reduced the reaction time drastically

  微波辐射已被用于加速靛红 (1a) 和 5-硝基靛红 (1b) 转化为它们的希夫碱 3-[5'-芳基(烷基)-2',4'-二氢-1',2', 4'-triazol-3'-on-4'-yl]iminoisatin (3a–g) 和 3-[5'-aryl(烷基)-2',4'-dihydro-1',2',4'- triazol-3'-on-4'-yl]imino-5-nitroisatin (4a–g) 分别。反应采用微波诱导技术，与传统加热相比，大大缩短了反应时间，提高了产率。新合成的碱基对所测试的标准细菌和真菌生物显示出中等的抗菌活性
• Synthesis, Molecular Docking Studies, Antimicrobial, Anticancer and Antioxidant Activity of Some Novel Mannich Bases of Isatin Scaffold
  作者：Kurni Lakshmi Deepthi、N.J.P. Subhashini、T. Maneshwar

  DOI：10.14233/ajchem.2022.23561

  日期：——

  A series of novel Mannich bases of isatin derivatives (VIIIa-VIIIt) was synthesized and evaluated as potential antimicrobial, antioxidant, anticancer activities and molecular docking studies. Structure of all the isatin derivatives was evaluated by IR, 1H NMR and mass spectral analysis. The antimicrobial activity results indicated that compounds VIIIb, VIIIi, VIIIm and VIIIo showed good activity in comparison to the activities of the standard molecules. Further, all isatin derivatives (VIIIa-VIIIt) have studied for their antioxidant activity by using ferric reducing antioxidant power assay (FRAP) method. Most of the synthesized compounds exhibited the significant antioxidant activities. The anticancer activity results suggested that the isatin derivatives VIIIm and VIIIg show the more activity against MCF-7 cells in comparison with doxorubicin as standard drug. Furthermore, the molecular docking studies of Mannich bases of isatin derivatives showed good agreement with the biological results when their binding pattern and affinity towards the active site of EGFR was inquisition.

  一系列新颖的异喹啉衍生物曼尼希碱（VIIIa-VIIIt）被合成并评估其作为潜在抗菌、抗氧化、抗癌活性和分子对接研究。所有异喹啉衍生物的结构均通过红外线、1H NMR和质谱分析进行评估。抗菌活性结果表明，化合物VIIIb、VIIIi、VIIIm和VIIIo的活性比标准分子高。此外，通过使用铁还原抗氧化功率（FRAP）法研究了所有异喹啉衍生物（VIIIa-VIIIt）的抗氧化活性。大多数合成化合物表现出显著的抗氧化活性。抗癌活性结果表明，异喹啉衍生物VIIIm和VIIIg对MCF-7细胞的活性比多柔比星标准药物更高。此外，异喹啉衍生物曼尼希碱的分子对接研究显示，它们与EGFR活性位点的结合模式和亲和力与生物学结果相符。
• Discovery of Tryptanthrin and Its Derivatives and Its Activities against NSCLC In Vitro via Both Apoptosis and Autophagy Pathways
  作者：Yayu Zou、Guanglong Zhang、Chengpeng Li、Haitao Long、Danping Chen、Zhurui Li、Guiping Ouyang、Wenjing Zhang、Yi Zhang、Zhenchao Wang

  DOI：10.3390/ijms24021450

  日期：——

  increased the expression of p21 in the A549 cells, inducing cell cycle arrest in the G2/M phase in a dose dependent manner. The further mechanism study found that C1 markedly increased the transformation from LC3-I to LC3-II. Taken together, our results suggest that C1 is capable of inhibiting the proliferation of non-small cell lung cancer (NSCLC) cells, inducing cell apoptosis, and triggering autophagy

  在这项研究中，合成了一系列新型色胺酮衍生物，并评估了它们对选定的人类癌细胞系，即肺癌 (A549)、慢性粒细胞白血病 (K562)、前列腺 (PC3) 和活细胞 (HepG2) 的抑制活性使用甲基噻唑基四唑鎓比色法 (MTT) 测定。在测试的化合物中，化合物 C1 对 A549 细胞系表现出良好的抑制作用，IC50 值为 0.55 ± 0.33 µM。通过细胞迁移实验观察细胞形态学结果表明，C1处理可显着抑制A549细胞的迁移。此外，经C1处理后，A549细胞表现出典型的凋亡形态和明显的自噬。此外，细胞凋亡和线粒体膜电位的检测表明，C1通过调节Bcl2家族成员的水平并破坏线粒体膜电位来诱导A549细胞凋亡。化合物C1还抑制细胞周期蛋白D1的表达并增加A549细胞中p21的表达，以剂量依赖的方式诱导细胞周期停滞在G2/M期。进一步的机制研究发现，C1 显着增加了从 LC3-I 到 LC3-II