3-(4-硝基苯胺基)-3-氧代丙酸甲酯 | 328011-26-3

• 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-硝基苯胺基)-3-氧代丙酸甲酯
• 英文名称: methyl 3-[(4-nitrophenyl)amino]-3-oxopropanoate
• 英文别名: Methyl 3-(4-nitroanilino)-3-oxopropanoate
• CAS: 328011-26-3
• 化学式: C₁₀H₁₀N₂O₅
• 分子量: 238.2
• InChiKey: NMGFQMDTGKOJGE-UHFFFAOYSA-N

物化性质

• 沸点：
  467.0±30.0 °C(Predicted)
• 密度：
  1.394±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  17
• 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：
  101
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3-(4-硝基苯胺基)-3-氧代丙酸甲酯 在 对甲苯磺酰叠氮 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 乙腈 为溶剂， 反应 15.0h， 以73%的产率得到methyl 2-diazo-3-[(4-nitrophenyl)amino]-3-oxopropanoate
  参考文献：
  名称：

  Studies towards the Synthesis of AlkylN-(4-Nitrophenyl)-3/2-oxomorpholine-2/3-carboxylates

  摘要：

  AbstractThe syntheses of methyl 4‐(4‐nitrophenyl)‐3‐oxomorpholine‐2‐carboxylate (3a) and ethyl 4‐(4‐nitrophenyl)‐2‐oxomorpholine‐3‐carboxylate (5b), important building blocks for the synthesis of factor Xa inhibitor rivaroxaban analogs with potential dual antithrombotic activity, via Rh2(OAc)4‐catalyzed OH and NH carbene insertion reactions are described.

  DOI：

  10.1002/hlca.201300085
• 作为产物：
  描述：

  丙二酸甲酯酰氯 、 4-硝基苯胺 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以74%的产率得到3-(4-硝基苯胺基)-3-氧代丙酸甲酯
  参考文献：
  名称：

  乙酸铑（II）催化OH和NH卡宾插入合成N-（4-硝基苯基）-3 / 2-氧吗啉-2 / 3-羧酸烷基酯

  摘要：

  甲基的合成ñ - （4-硝基苯基）-3-氧代吗啉-2-羧酸乙酯和ñ - （4-硝基苯基）-2-氧代吗啉-3-羧酸乙酯，通过铑（II），乙酸催化分子间O - H和分子内描述了N–H卡宾的插入。该产品代表了用于合成具有药物意义的生物活性化合物的新型多功能部件。

  DOI：

  10.1016/j.tetlet.2013.04.049

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。
• 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.
• 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.