3-(4-氨基苯胺基)-3-氧代丙酸甲酯 | 325168-04-5

• 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: 3-(4-氨基苯胺基)-3-氧代丙酸甲酯
• 英文名称: methyl 3-((4-aminophenyl)amino)-3-oxopropanoate
• 英文别名: N-(4-amino-phenyl)-malonamic acid methyl ester；Methyl 3-(4-aminoanilino)-3-oxopropanoate
• CAS: 325168-04-5
• 化学式: C₁₀H₁₂N₂O₃
• 分子量: 208.217
• InChiKey: AMBNNUHYEFBYNF-UHFFFAOYSA-N

物化性质

• 沸点：
  344.7±22.0 °C(Predicted)
• 密度：
  1.290±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  81.4
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-(4-氨基苯胺基)-3-氧代丙酸甲酯 在 lithium hydroxide 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 水 为溶剂， 生成 N-(4-Methanesulfonylamino-phenyl)-malonamic acid
  参考文献：
  名称：

  Novel malonamide derivatives as potent κ opioid receptor agonists

  摘要：

  A novel series of malonamide derivatives was synthesized. These amides were shown to be potent and selective kappa opioid receptor agonists. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2007.01.053
• 作为产物：
  描述：

  3-(4-硝基苯胺基)-3-氧代丙酸甲酯 在 palladium on activated charcoal 、 氢气 作用下， 以 四氢呋喃 为溶剂， 反应 3.0h， 以58%的产率得到3-(4-氨基苯胺基)-3-氧代丙酸甲酯
  参考文献：
  名称：

  New N -phenyl-4,5-dibromopyrrolamides and N -Phenylindolamides as ATPase inhibitors of DNA gyrase

  摘要：

  Following the withdrawal of novobiocin, the introduction of a new ATPase inhibitor of DNA gyrase to the clinic would add the first representative of this mechanistic class to the antibacterial pipeline. This would be of great importance because of the well-known problems associated with antibacterial resistance. Using structure-based design and starting from the recently determined crystal structure of the N-phenyl-4,5-dibromopyrrolamide inhibitor-DNA gyrase B complex, we have prepared 28 new N-phenyl-4,5-dibromopyrrolamides and N-phenylindolamides and evaluated them against DNA gyrase from Escherichia coli. The most potent compound was 2-((4-(4,5-dibromo-1H-pyrrole-2-carboxamido)phenyl) amino)-2-oxoacetic acid (9a), with an IC50 of 0.18 mu M against E. coli gyrase. A selected set of compounds was evaluated against DNA gyrase from Staphylococcus aureus and against topoisomerase IV from E. coli and S. aureus, but the activities were weaker. The binding affinity of 2-((4-(4,5-dibromo-1H-pyrrole-2carboxamido)phenyl)amino)-2-oxoacetic acid (9a) to E. coli gyrase was studied using surface plasmon resonance. In the design of the present series, the focus was on the optimisation of biological activities of compounds especially by varying their size, the position and orientation of key functional groups, and their acid base properties. The structure activity relationship (SAR) was examined and the results were rationalised with molecular docking. (C) 2016 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2016.03.079

文献信息

• Amide derivatives and methods of their use
  申请人：Dolle E. Roland

  公开号：US20050107355A1

  公开（公告）日：2005-05-19

  Amide derivatives of the general formulae Ia and Ib: are disclosed. Pharmaceutical compositions containing these compounds, and methods for their use, inter alia, for treating and/or preventing gastrointestinal disorders, pain, and pruritus are also disclosed.

  一般式Ia和Ib的酰胺衍生物已被披露。还披露了含有这些化合物的药物组合物，以及用于治疗和/或预防胃肠道疾病、疼痛和瘙痒等的方法。
• US7160902B2
  申请人：——

  公开号：US7160902B2

  公开（公告）日：2007-01-09
• [EN] AMIDE DERIVATIVES AND METHODS OF THEIR USE<br/>[FR] DERIVES D'AMIDE ET LEURS PROCEDES D'UTILISATION
  申请人：ADOLOR CORP

  公开号：WO2005049564A1

  公开（公告）日：2005-06-02

  Amide derivatives of the general formulae Ia and Ib are disclosed. Pharmaceutical compositions containing these compounds, and methods for their use, inter alia, for treating and/or preventing gastrointestinal disorders, pain, and pruritus are also disclosed.
• New N -phenyl-4,5-dibromopyrrolamides and N -Phenylindolamides as ATPase inhibitors of DNA gyrase
  作者：Nace Zidar、Tihomir Tomašič、Helena Macut、Anja Sirc、Matjaž Brvar、Sofia Montalvão、Päivi Tammela、Janez Ilaš、Danijel Kikelj

  DOI：10.1016/j.ejmech.2016.03.079

  日期：2016.7

  Following the withdrawal of novobiocin, the introduction of a new ATPase inhibitor of DNA gyrase to the clinic would add the first representative of this mechanistic class to the antibacterial pipeline. This would be of great importance because of the well-known problems associated with antibacterial resistance. Using structure-based design and starting from the recently determined crystal structure of the N-phenyl-4,5-dibromopyrrolamide inhibitor-DNA gyrase B complex, we have prepared 28 new N-phenyl-4,5-dibromopyrrolamides and N-phenylindolamides and evaluated them against DNA gyrase from Escherichia coli. The most potent compound was 2-((4-(4,5-dibromo-1H-pyrrole-2-carboxamido)phenyl) amino)-2-oxoacetic acid (9a), with an IC50 of 0.18 mu M against E. coli gyrase. A selected set of compounds was evaluated against DNA gyrase from Staphylococcus aureus and against topoisomerase IV from E. coli and S. aureus, but the activities were weaker. The binding affinity of 2-((4-(4,5-dibromo-1H-pyrrole-2carboxamido)phenyl)amino)-2-oxoacetic acid (9a) to E. coli gyrase was studied using surface plasmon resonance. In the design of the present series, the focus was on the optimisation of biological activities of compounds especially by varying their size, the position and orientation of key functional groups, and their acid base properties. The structure activity relationship (SAR) was examined and the results were rationalised with molecular docking. (C) 2016 Elsevier Masson SAS. All rights reserved.
• Novel malonamide derivatives as potent κ opioid receptor agonists
  作者：Guo-Hua Chu、Minghua Gu、Joel A. Cassel、Serge Belanger、Thomas M. Graczyk、Robert N. DeHaven、Nathalie Conway-James、Michael Koblish、Patrick J. Little、Diane L. DeHaven-Hudkins、Roland E. Dolle

  DOI：10.1016/j.bmcl.2007.01.053

  日期：2007.4

  A novel series of malonamide derivatives was synthesized. These amides were shown to be potent and selective kappa opioid receptor agonists. (c) 2007 Elsevier Ltd. All rights reserved.