2-(2-(2,6-dichlorophenylamino)phenyl)acetohydrazide | 133239-50-6

• 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: 2-(2-(2,6-dichlorophenylamino)phenyl)acetohydrazide
• 英文别名: [2-(2,6-dichloroanilino)phenyl]acetic acid hydrazide；diclofenac hydrazide；2-[2-(2,6-dichloroanilino)phenyl]acetohydrazide；2-[(2,6-Dichlorophenyl)amino]benzeneacetic acid, hydrazide
• CAS: 133239-50-6
• 化学式: C₁₄H₁₃Cl₂N₃O
• 分子量: 310.183
• InChiKey: MNEGZEJTFZVUDN-UHFFFAOYSA-N

物化性质

• 熔点：
  134-136 °C(Solvent: Ethanol)
• 沸点：
  486.2±45.0 °C(Predicted)
• 密度：
  1.398±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  67.2
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(2-(2,6-dichlorophenylamino)phenyl)acetohydrazide 在 溶剂黄146 、 potassium hydroxide 作用下， 以 乙醇 为溶剂， 反应 12.0h， 生成 (E)-3-(2-(2,6-dichlorophenylamino)benzyl)-1-(piperidin-1-ylmethyl)-4-(thiophen-2-ylmethyleneamino)-1H-1,2,4-triazole-5(4H)-thione
  参考文献：
  名称：

  新型含1,2,4-三唑类潜在抗结核药的二苯胺的设计，合成和3D-QSAR研究

  摘要：

  由4-亚芳基氨基-5- [2-（2,6-二氯苯基氨基）苄基] -2H-1,2,4-三唑-3（4H）合成了一系列新的含1,2,4-三唑的新二苯胺-硫酮3a – f。筛选合成的化合物的体外抗分枝杆菌和抗菌活性。合成的化合物4a，4e和4d已经显示出针对分别为0.2、1.6和3.125μM的MIC的结核分枝杆菌H 37 Rv菌株的潜在活性。为了更详细地研究含1,2,4-三唑衍生物的二苯胺的SAR，CoMFA（q 2 -0.432，r2 -0.902）和CoMSIA（q 2 -0.511，- [R 2 -0.953）上的模型中号。建立了结核病H 37 Rv。生成的3D-QSAR模型在外部进行了验证，并显示出显着的统计结果，这些模型可用于进一步合理设计含有1,2,4-三唑类作为有效抗结核药的新型二苯胺。

  DOI：

  10.1016/j.ejmech.2014.07.051
• 作为产物：
  描述：

  双氯芬酸 在 氯化亚砜 、 一水合肼 作用下， 以 乙醇 、 丙酮 为溶剂， 反应 6.0h， 生成 2-(2-(2,6-dichlorophenylamino)phenyl)acetohydrazide
  参考文献：
  名称：

  Diclofenac derivatives as concomitant inhibitors of cholinesterase, monoamine oxidase, cyclooxygenase-2 and 5-lipoxygenase for the treatment of Alzheimer's disease: synthesis, pharmacology, toxicity and docking studies

  摘要：

  同时靶向胆碱酯酶（ChEs）和单胺氧化酶（MAO-A 和 MAO-B）是治疗多因素阿尔茨海默病（AD）的关键策略之一。

  DOI：

  10.1039/d2ra04183a

文献信息

• PHTHALIMIDE DERIVATIVES OF NON-STEROIDAL ANTI-INFLAMMATORY COMPOUNDS AND/OR TNF-ALPHA MODULATORS, METHOD FOR PRODUCING SAME, PHARMACEUTICAL COMPOSITIONS CONTAINING SAME AND USES THEREOF FOR THE TREATMENT OF INFLAMMATORY DISEASES
  申请人：dos Santos Jean Leandro

  公开号：US20120115817A1

  公开（公告）日：2012-05-10

  The present invention relates to phthalimide derivatives of non-steroidal and/or TNF-α modulating anti-inflammatory compounds as well as the process of obtaining the so-called derivatives, pharmaceutical compositions containing such derivatives and their uses, including use in the treatment of inflammatory diseases, especially those related to chronic inflammatory processes, such as rheumatoid arthritis and intestinal inflammatory diseases (for instance, Chron's disease) and the use of the referred to pharmaceutical compositions as antipyretic, analgesic and platelet antiaggregating medications.

  本发明涉及非甾体和/或调节肿瘤坏死因子-α（TNF-α）的抗炎化合物的酞酰亚胺衍生物，以及获得所述衍生物的方法、包含该衍生物的药物组合物及其用途，包括用于治疗炎症疾病，尤其是与慢性炎症过程相关的疾病，例如类风湿性关节炎和肠道炎症疾病（例如，克罗恩病），以及将所述药物组合物用作退热剂、镇痛剂和抗血小板聚集药物的使用。
• Design, Synthesis and QSAR Studies on a Series of 2, 5-Disubstituted- 1,3,4-oxadiazole Derivatives of Diclofenac and Naproxen for Analgesic and Anti-inflammatory Activity
  作者：Kaliappan Ilango、Parthiban Valentina、Gajendra Kumar、Dushyant Dixit、Shrikant Nilewar、Muthu Kathiravan

  DOI：10.2174/1573406411666150519112037

  日期：2015.10.29

  A series of twenty molecules belonging to 2,5-disubstituted-1,3,4-oxadiazole derivatives of Diclofenac and Naproxen were designed, synthesized and their structures were confirmed by spectroscopy. The target compounds were evaluated for anti-inflammatory and analgesic activity. The result indicates that the compounds 12, 4, 6, 7 and 15 were found to have good analgesic and anti-inflammatory activities, while the compounds 12 and 14 were found to have good analgesic and the compound 22 were found to have good anti-inflammatory activities. HQSAR and Topomer QSAR studies were performed to get insights in the structures contributing for biological activity. The compounds bearing mono-substitution such as Cl, OCH3 and NO2 in the phenyl ring were found to have maximum analgesic and anti-inflammatory activities

  设计、合成了属于双氯芬酸和萘普生衍生物的2,5-二取代-1,3,4-噁二唑系列二十种分子，并通过光谱学确认其结构。对目标化合物进行了抗炎和镇痛活性的评估。结果表明，化合物12、4、6、7和15具有良好的镇痛和抗炎活性，而化合物12和14具有良好的镇痛活性，化合物22具有良好的抗炎活性。进行了HQSAR和Topomer QSAR研究，以深入了解对生物活性有贡献的结构因素。发现苯环上单取代如Cl、OCH3和NO2的化合物具有最高的镇痛和抗炎活性。
• Synthesis and anti-inflammatory, analgesic, ulcerogenic and lipid peroxidation activities of some new 2-[(2,6-dichloroanilino) phenyl]acetic acid derivatives
  作者：Mohd Amir、Kumar Shikha

  DOI：10.1016/j.ejmech.2004.02.008

  日期：2004.6

  The synthesis of a group of 1,3,4-oxadiazoles, 1,2,4-triazoles, 1,3,4-thiadiazoles and 1,2,4-triazine derived from 2-[(2,6-dichloroanilino) phenyl] acetic acid is described. The structures of new compounds are supported by IR, (1)H-NMR and Mass spectral data. These compounds were tested in vivo for their anti-inflammatory activity. The compounds, which showed activity comparable to the standard drug

  由2-[（2,6-二氯苯胺基）苯基衍生的一组1,3,4-恶二唑，1,2,4-三唑，1,3,4-噻二唑和1,2,4-三嗪的合成描述了乙酸。IR，（1）H-NMR和质谱数据支持了新化合物的结构。在体内测试了这些化合物的抗炎活性。筛选显示出与标准双氯芬酸相当的活性的化合物的镇痛，促溃疡和脂质过氧化活性。28种化合物中的10种新化合物在角叉菜胶诱导的大鼠爪水肿试验中显示出非常好的抗炎活性，在乙酸诱导的扭体试验中具有显着的止痛活性，而致溃疡作用却可以忽略不计。这些化合物显示出较少的致溃疡作用，还显示出丙二醛含量（MDA）降低，这是脂质过氧化作用的副产物之一。研究表明，这些化合物抑制了胃粘膜病变的诱导，从我们的结果可以看出，它们的保护作用可能与抑制胃粘膜脂质过氧化有关。
• Synthesis and evaluation of anti-inflammatory and analgesic activity of 3-[(5-substituted-1,3,4-oxadiazol-2-yl-thio)acetyl]-2H-chromen-2-ones
  作者：Nista Ingale、Veeresh Maddi、Mahesh Palkar、Pradeepkumar Ronad、Shivalingrao Mamledesai、A. H. M. Vishwanathswamy、Darbhamulla Satyanarayana

  DOI：10.1007/s00044-010-9494-z

  日期：2012.1

  physicochemical, elemental analysis, and spectral data. The title compounds were screened for in vivo acute anti-inflammatory and analgesic activities at a dose of 200 mg/kg bw. Among the series, four compounds 7c, 7e, 7f, and 7h were found to possess a significant anti-inflammatory and analgesic activity profile. In addition, these compounds were also found to possess a less degree of ulcerogenic potential

  通过适当取代基之间的缩合反应合成了一系列新的3-[（5-取代-1,3,4-恶二唑-2-基-硫基）乙酰基] -2H-铬-2--2-酮（7a – i）。来自多种现有NSAID的5-取代的1,3,4-恶二唑基-2-硫酮（4a – i）和3-（2-溴乙酰基）-2H-铬-2--2-酮（6）在存在下回流下乙醇钠。根据理化，元素分析和光谱数据确定了合成化合物的结构。以200mg / kg体重的剂量筛选标题化合物的体内急性抗炎和镇痛活性。在该系列中，四种化合物7c，7e，7f发现7h和7h具有明显的抗炎和镇痛活性。另外，与标准的NSAID相比，还发现这些化合物具有较小程度的致溃疡潜力。
• Diclofenac-Based Hydrazones and Spirothiazolidinones: Synthesis, Characterization, and Antimicrobial Properties
  作者：Ayşe Kocabalkanlı、Gökçe Cihan-Üstündağ、Lieve Naesens、Emel Mataracı-Kara、Mebble Nassozi、Gültaze Çapan

  DOI：10.1002/ardp.201700010

  日期：2017.5

  We report here the synthesis, structural characterization, and biological evaluation of novel diclofenac‐based hydrazone (4a–f) and spirothiazolidinone (5a–f, 6a–f) derivatives designed as potential antimicrobial agents. The compounds were evaluated in vitro for their antiviral activity against a wide spectrum of DNA and RNA viruses. They were further screened in vitro against different strains of

  我们在此报告了设计为潜在抗菌剂的新型双氯芬酸腙（4a-f）和螺噻唑烷酮（5a-f，6a-f）衍生物的合成、结构表征和生物学评价。在体外评估了这些化合物对广泛的 DNA 和 RNA 病毒的抗病毒活性。它们在体外针对不同的细菌和真菌菌株进行了进一步筛选。发现腙衍生物 4a 和 4c-f 对疱疹病毒（HSV-1、HSV-2 和 HSV-1 TK-）、痘苗病毒和柯萨奇 B4 病毒具有活性，EC50 值在 6.6 µg/mL 之间和 14.7 μg/mL，4a 和 4f 的选择性指数值均大于 10。新合成的化合物 (4-6) 对测试的细菌和真菌菌株无活性，浓度低于 2500、1250 或 625 μg/mL。有趣的是，