4-(2-hydroxyimino-acetylamino)-benzoic acid | 17122-78-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 4-(2-hydroxyimino-acetylamino)-benzoic acid
• 英文别名: 4-(2-Hydroxyimino-acetylamino)-benzoesaeure；4-(Hydroxyimino-acetamino)-benzoesaeure；4-(α-Oximino-acetamino)-benzoesaeure；4'-Carboxyisonitrosoacetanilid；4-Carboxyisonitrosoacetanilid；4-[2-(N-hydroxyimino)acetamido]benzoic acid；4-[(2-hydroxyiminoacetyl)amino]benzoic acid
• CAS: 17122-78-0
• 化学式: C₉H₈N₂O₄
• 分子量: 208.174
• InChiKey: SDTJRMCHWCUSBN-UHFFFAOYSA-N

物化性质

• 熔点：
  147 °C
• 密度：
  1.41±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  99
• 氢给体数：
  3
• 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：

  4-(2-hydroxyimino-acetylamino)-benzoic acid 在 hydrazine hydrate 、 硫酸 作用下， 生成 5-羧基吲哚-2-酮
  参考文献：
  名称：

  Synthesis, anti-lung cancer activity and molecular docking study of 3-methylene-2-oxoindoline-5-carboxamide derivatives

  摘要：

  A series of 3-methylene-2-oxoindoline-5-carboxamide derivatives were synthesized in appreciable yield by using 4-aminobenzoic acid as a starting material. The preliminary biological test results showed that most compounds displayed potent inhibitory activity against proliferation of human lung adenocarcinoma epithelial cell line (A549) in MTT assay. Compound 6l displayed the highest potency (IC50 = 3.0 mu M). The western blot analysis demonstrated a correlation between anti-proliferative activity of active compounds and blockade of the phosphorylation of extracellular signal-regulated kinases (ERK1/2). The docking study also provides new insights into further optimization of 3-methylene-2-oxoindoline-5-carboxamide derivatives for the discovery of more potent RAF/MEK/ERK pathway regulators as anti-lung cancer agents.

  DOI：

  10.1007/s00044-017-2050-3
• 作为产物：
  描述：

  对氨基苯甲酸 在 水合氯醛 、 盐酸羟胺 、 sodium sulfate 作用下， 生成 4-(2-hydroxyimino-acetylamino)-benzoic acid
  参考文献：
  名称：

  Synthesis and cytotoxicity of novel indirubin-5-carboxamides

  摘要：

  Indirubins have been reported to act as potent inhibitors of protein kinases relevant to tumorigenesis and of tumor cell growth, but their development to antitumor drugs suffer from their poor water solubility. We synthesized a novel class of indirubin derivatives, indirubin-5-carboxamides, carrying amide substituents with basic centers. Quaternization or protonation of these alkylamino substituents provided indirubins with significantly improved solubility without loss of bioactivity. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.04.066

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。
• Waldmann, Journal fur praktische Chemie (Leipzig 1954), 1937, vol. <2> 147, p. 338,340
  作者：Waldmann

  DOI：——

  日期：——
• Synthesis and cytotoxicity of novel indirubin-5-carboxamides
  作者：Xinlai Cheng、Paul Rasqué、Sandra Vatter、Karl-Heinz Merz、Gerhard Eisenbrand

  DOI：10.1016/j.bmc.2010.04.066

  日期：2010.6.15

  Indirubins have been reported to act as potent inhibitors of protein kinases relevant to tumorigenesis and of tumor cell growth, but their development to antitumor drugs suffer from their poor water solubility. We synthesized a novel class of indirubin derivatives, indirubin-5-carboxamides, carrying amide substituents with basic centers. Quaternization or protonation of these alkylamino substituents provided indirubins with significantly improved solubility without loss of bioactivity. (C) 2010 Elsevier Ltd. All rights reserved.
• Synthesis, anti-lung cancer activity and molecular docking study of 3-methylene-2-oxoindoline-5-carboxamide derivatives
  作者：Juntao Ai、Meng Lv、Xiaohui Li、Zhuo Chen、Gaoyun Hu、Qianbin Li

  DOI：10.1007/s00044-017-2050-3

  日期：2018.1

  A series of 3-methylene-2-oxoindoline-5-carboxamide derivatives were synthesized in appreciable yield by using 4-aminobenzoic acid as a starting material. The preliminary biological test results showed that most compounds displayed potent inhibitory activity against proliferation of human lung adenocarcinoma epithelial cell line (A549) in MTT assay. Compound 6l displayed the highest potency (IC50 = 3.0 mu M). The western blot analysis demonstrated a correlation between anti-proliferative activity of active compounds and blockade of the phosphorylation of extracellular signal-regulated kinases (ERK1/2). The docking study also provides new insights into further optimization of 3-methylene-2-oxoindoline-5-carboxamide derivatives for the discovery of more potent RAF/MEK/ERK pathway regulators as anti-lung cancer agents.