ethyl 3-amino-4-(phenylamino)benzoate | 68765-57-1

• 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: ethyl 3-amino-4-(phenylamino)benzoate
• 英文别名: ethyl3-amino-4-(phenylamino)benzoate；SRS8-42；3-amino-4-anilino-benzoic acid ethyl ester；3-Amino-4-anilino-benzoesaeure-aethylester；Ethyl 3-amino-4-anilinobenzoate
• CAS: 68765-57-1
• 化学式: C₁₅H₁₆N₂O₂
• 分子量: 256.304
• InChiKey: CMXUAKNOWBZBKA-UHFFFAOYSA-N

物化性质

• 熔点：
  75-76 °C
• 沸点：
  423.4±35.0 °C(Predicted)
• 密度：
  1.208±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  64.4
• 氢给体数：
  2
• 氢受体数：
  4

安全信息

• 危险等级：
  IRRITANT

反应信息

• 作为反应物：
  描述：

  ethyl 3-amino-4-(phenylamino)benzoate 、 sodium hydroxy(4-methoxyphenyl)methanesulfonate 以 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 以80%的产率得到ethyl 2-(4-methoxyphenyl)-1-phenyl-1H-benzo[d]imida-zole-5-carboxylate
  参考文献：
  名称：

  Antituberculosis agents bearing the 1,2-disubstituted benzimidazole scaffold

  摘要：

  The emergence of drug-resistant strains in recent years has fueled the epidemic of tuberculosis. This necessitates the development of new chemical scaffolds to curb resistant tuberculosis for effective control of this disease. In this study, we have designed and synthesized two series of benzimidazole derivatives. Their antimycobacterial activities were initially evaluated using Mycobacterium tuberculosis H37RV strains. The most potent analog (6h) was further assessed using various drug-resistant M. tuberculosis strains. This report described the importance of benzimidazoles as new antitmycobacterial agents targeting both the M. tuberculosis H37RV as well as the drug-resistant-tuberculosis strains. The trifluoromethyl group which was essential for antimycobacterial activity was also highlighted.

  DOI：

  10.1007/s00044-017-1784-2
• 作为产物：
  描述：

  ethyl 3-nitro-4-(phenylamino)benzoate 在 palladium 10% on activated carbon 、 甲酸铵 作用下， 以 乙醇 为溶剂， 以71%的产率得到ethyl 3-amino-4-(phenylamino)benzoate
  参考文献：
  名称：

  通过多步合成对苯并咪唑进行结构修饰及其对 Sirtuin 抑制活性的影响

  摘要：

  苯并咪唑衍生物已被证明具有抑制沉默调节蛋白的活性。在不断寻找有效的sirtuin抑制剂的过程中，对先前鉴定的苯并咪唑类sirtuin抑制剂末端苯环进行了系统的改变，以进一步研究它们的构效关系。结果表明，这些新化合物的sirtuin活性遵循除卤代取代基外，间位取代化合物的效力明显弱于邻位和对位取代化合物的趋势。进行分子对接研究以使这些观察合理化。除此之外，还讨论了用于合成有趣化合物的方法。

  DOI：

  10.1002/ardp.201500337

文献信息

• [EN] COMPOUNDS, COMPOSITIONS, AND METHODS FOR MODULATING FERROPTOSIS AND TREATING EXCITOTOXIC DISORDERS<br/>[FR] COMPOSÉS, COMPOSITIONS, ET PROCÉDÉS POUR MODULER LA FERROPTOSE ET TRAITER DES TROUBLES EXCITOTOXIQUES
  申请人：UNIV COLUMBIA

  公开号：WO2013152039A1

  公开（公告）日：2013-10-10

  The present invention provides, inter alia, a compound having the structure: (Formula (I). Also provided are compositions containing a pharmaceutically acceptable carrier and a compound according to the present invention. Further provided are methods for treating or ameliorating the effects of an excitotoxic disorder in a subject, methods of modulating ferroptosis in a subject, methods of reducing reactive oxygen species (ROS) in a cell, and methods for treating or ameliorating the effects of a neurodegenerative disease.

  本发明提供了一种具有以下结构的化合物：（化学式（I）。还提供了含有药用载体和根据本发明的化合物的组合物。进一步提供了用于治疗或改善受体内兴奋毒性障碍影响的方法，用于调节受体内铁死亡的方法，用于减少细胞内活性氧化物种（ROS）的方法，以及用于治疗或改善神经退行性疾病影响的方法。
• [EN] MODULATING FERROPTOSIS AND TREATING EXCITOTOXIC DISORDERS<br/>[FR] MODULATION DE LA FERROPTOSE ET TRAITEMENT DES TROUBLES EXCITOTOXIQUES
  申请人：UNIV COLUMBIA

  公开号：WO2015084749A1

  公开（公告）日：2015-06-11

  The present invention provides, inter alia, a compound having the structure of Formula (I). Also provided are compositions containing a pharmaceutically acceptable carrier and a compound according to the present invention. Further provided are methods for treating or ameliorating the effects of an excitotoxic disorder in a subject, methods of modulating ferroptosis in a subject, methods of reducing reactive oxygen species (ROS) in a cell, and methods for treating or ameliorating the effects of a neurodegenerative disease.

  本发明提供了一种具有式（I）结构的化合物。还提供了含有药用载体和根据本发明的化合物的组合物。此外还提供了用于治疗或改善受体内兴奋毒性障碍影响的方法，用于调节受体内铁死亡的方法，用于减少细胞内活性氧化物种（ROS）的方法，以及用于治疗或改善神经退行性疾病影响的方法。
• Structural Modifications of Benzimidazoles via Multi-Step Synthesis and Their Impact on Sirtuin-Inhibitory Activity
  作者：Yeong Keng Yoon、Tan Soo Choon

  DOI：10.1002/ardp.201500337

  日期：2016.1

  Benzimidazole derivatives have been shown to possess sirtuin‐inhibitory activity. In the continuous search for potent sirtuin inhibitors, systematic changes on the terminal benzene ring were performed on previously identified benzimidazole‐based sirtuin inhibitors, to further investigate their structure–activity relationships. It was demonstrated that the sirtuin activities of these novel compounds

  苯并咪唑衍生物已被证明具有抑制沉默调节蛋白的活性。在不断寻找有效的sirtuin抑制剂的过程中，对先前鉴定的苯并咪唑类sirtuin抑制剂末端苯环进行了系统的改变，以进一步研究它们的构效关系。结果表明，这些新化合物的sirtuin活性遵循除卤代取代基外，间位取代化合物的效力明显弱于邻位和对位取代化合物的趋势。进行分子对接研究以使这些观察合理化。除此之外，还讨论了用于合成有趣化合物的方法。
• Compounds, Compositions, and Methods For Modulating Ferroptosis and Treating Excitotoxic Disorders
  申请人：The Trustees of Columbia University in the City of New York

  公开号：US20150079035A1

  公开（公告）日：2015-03-19

  The present invention provides, inter alia, a compound having the structure: (Formula (I). Also provided are compositions containing a pharmaceutically acceptable carrier and a compound according to the present invention. Further provided are methods for treating or ameliorating the effects of an excitotoxic disorder in a subject, methods of modulating ferroptosis in a subject, methods of reducing reactive oxygen species (ROS) in a cell, and methods for treating or ameliorating the effects of a neurodegenerative disease.

  本发明提供了一种具有以下结构的化合物：（公式（I）。还提供了含有药用载体和本发明中所述化合物的组合物。此外，还提供了治疗或改善受体中兴奋毒性障碍影响的方法，调节受体中铁死亡的方法，降低细胞中反应性氧化物（ROS）的方法，以及治疗或改善神经退行性疾病影响的方法。
• Compounds, compositions, and methods for modulating ferroptosis and treating excitotoxic disorders
  申请人：THE TRUSTEES OF COLUMBIA UNIVERSITY IN THE CITY OF NEW YORK

  公开号：US10233171B2

  公开（公告）日：2019-03-19

  The present invention provides, inter alia, a compound having the structure: Also provided are compositions containing a pharmaceutically acceptable carrier and a compound according to the present invention. Further provided are methods for treating or ameliorating the effects of an excitotoxic disorder in a subject, methods of modulating ferroptosis in a subject, methods of reducing reactive oxygen species (ROS) in a cell, and methods for treating or ameliorating the effects of a neurodegenerative disease.

  本发明特别提供了一种具有以下结构的化合物： 还提供了含有药学上可接受的载体和根据本发明的化合物的组合物。本发明还提供了治疗或改善受试者兴奋性中毒症的方法、调节受试者铁变态反应的方法、减少细胞中活性氧（ROS）的方法，以及治疗或改善神经退行性疾病的方法。