3-硝基-4-(苯基氨基)苯甲酸甲酯 | 148304-23-8

• 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-硝基-4-(苯基氨基)苯甲酸甲酯
• 英文名称: 4-methoxycarbonyl-2-nitro-N-phenylaniline
• 英文别名: methyl 4-anilino-3-nitrobenzoate；methyl 2-nitrodiphenylamine-4-caarboxylate；methyl 4-(phenylamino)-3-nitrobenzoate；3-nitro-4-phenylaminobenzoic acid methyl ester；4-anilino-3-nitro-benzoic acid methyl ester；4-Anilino-3-nitro-benzoesaeure-methylester；Methyl 3-nitro-4-(phenylamino)benzoate
• CAS: 148304-23-8
• 化学式: C₁₄H₁₂N₂O₄
• 分子量: 272.26
• InChiKey: DYBDOVKHIAJFQP-UHFFFAOYSA-N

物化性质

• 熔点：
  127 °C
• 沸点：
  423.5±35.0 °C(Predicted)
• 密度：
  1.326±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 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：
  84.2
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3-硝基-4-(苯基氨基)苯甲酸甲酯 在 manganese(IV) oxide 、 palladium 10% on activated carbon 、 氯化锆(IV) 、 肼 作用下， 以 乙醇 为溶剂， 反应 1.08h， 生成 2-[(E)-2-(methylphenylamino)ethenyl]-1-phenyl-1H-benzoimidazole-5-carboxylic acid methyl ester
  参考文献：
  名称：

  Synthesis and Biological Evaluation of Analogues of AKT (Protein Kinase B) Inhibitor-IV

  摘要：

  Inhibitors of the PI3-kinase/AKT (protein kinase B) pathway are under investigation as anticancer and antiviral agents. The benzimidazole derivative AKT inhibitor-IV (ChemBridge 5233705) affects this pathway and exhibits potent anticancer and antiviral activity. To probe its biological activity, we synthesized AKT inhibitor-IV and 21 analogues using a novel six-step route based on ZrCl4-catalyzed cyclization of 1,2-arylenediamines with alpha,beta-unsaturated aldehydes. We examined effects on viability of HeLa carcinoma cells, viability of normal human cells (NHBE), replication of recombinant parainfluenza virus 5 (PIV5) in HeLa cells, and replication of the intracellular bacterium Mycobacterium fortuitum in HeLa cells. Replacement of the benzimidazole N-ethyl substitutent of AKT inhibitor-IV with N-hexyl and N-dodecyl groups enhanced antiviral activity and cytotoxicity against the cancer cell line, but these compounds showed substantially lower toxicity (from 6-fold to >20-fold) against NHBE cells and no effect on M. fortuitum, suggesting inhibition of one or more host protein(s) required for proliferation of cancer cells and PIV5. The key structural elements identified here may facilitate identification of targets of this highly biologically active scaffold.

  DOI：

  10.1021/jm100912b
• 作为产物：
  描述：

  4-氯-3-硝基苯甲酸 在 N-甲基吗啉 、 盐酸 、 铜 作用下， 以 异戊醇 为溶剂， 反应 36.0h， 生成 3-硝基-4-(苯基氨基)苯甲酸甲酯
  参考文献：
  名称：

  Structure−Activity Relationships for 1-Phenylbenzimidazoles as Selective ATP Site Inhibitors of the Platelet-Derived Growth Factor Receptor

  摘要：

  1-Phenylbenzimidazoles are shown to be a new class of ATP-site inhibitors of the platelet-derived growth factor receptor (PDGFR). Structure-activity relationships (SARs) are narrow, with closely related heterocycles being inactive. A systematic study of substituted 1-phenyl-benzimidazoles showed clear SARs. Substituents at the 4'- and 3'-positions of the phenyl ring are tolerated but do not significantly improve activity, while substituents at the 2'-position abolish it. Substituents in the 2-, 4-, and 7-positions of the benzimidazole ring (with the exception of 4-OH) also abolish activity. Most substituents at the 5- and B-positions maintain or increase activity, with the 5-OH, 5-OMe, 5-COMe, and 5-CO2Me analogues being >10-fold more potent than the parent 1-phenylbenzimidazole. The 5-OMe analogue was both the most potent inhibitor, and showed the highest selectivity (50-fold) between PDGFR and FGFR isolated enzymes, and also a moderately effective inhibitor (IC50 = 1.9 mu M) of PDGF-stimulated PDGFR autophosphorylation in rat aorta smooth muscle cells.

  DOI：

  10.1021/jm9804681

文献信息

• HETEROCYCLIC COMPOUNDS FOR THE INHIBITION OF PASK
  申请人：McCall John M.

  公开号：US20120225846A1

  公开（公告）日：2012-09-06

  Disclosed herein are new heterocyclic compounds and compositions and their application as pharmaceuticals for the treatment of disease. Methods of inhibiting PAS Kinase (PASK) activity in a human or animal subject are also provided for the treatment of diseases such as diabetes mellitus.

  本文披露了新的杂环化合物和组合物，以及它们作为药物治疗疾病的应用。还提供了抑制PAS激酶（PASK）在人类或动物主体中活性的方法，用于治疗疾病，如糖尿病。
• 3D-Printed Polypropylene Continuous-Flow Column Reactors: Exploration of Reactor Utility in S_N Ar Reactions and the Synthesis of Bicyclic and Tetracyclic Heterocycles
  作者：Zenobia X. Rao、Bhaven Patel、Alessandra Monaco、Zi Jing Cao、Marta Barniol-Xicota、Enora Pichon、Mark Ladlow、Stephen T. Hilton

  DOI：10.1002/ejoc.201701111

  日期：2017.12.1

  FlowSyn continuous-flow reactor. Reactor utility was explored in reactions ranging from SNAr reactions to formation of complex heterocycles. It was shown that they are an inexpensive source of reactors for continuous flow, facilitating the synthesis of a range of heterocycles.

  设计低成本的惰性聚丙烯（PP）连续流反应器并进行3D打印，以用于FlowSyn连续流反应器。在从S N Ar反应到复杂杂环形成的反应中探索了反应器的效用。结果表明，它们是连续流动反应器的廉价来源，可促进一系列杂环的合成。
• Stable and Easily Accessible Functional Dyes: Dihydrotetraazaanthracenes as Versatile Precursors for Higher Acenes
  作者：Dominique Mario Gampe、Martin Kaufmann、Dörthe Jakobi、Torsten Sachse、Martin Presselt、Rainer Beckert、Helmar Görls

  DOI：10.1002/chem.201500230

  日期：2015.5.11

  system. Relationships between the structure and the spectroscopic properties could be derived from UV/Vis absorption and fluorescence spectroscopy, as well as by DFT and TD‐DFT calculations of molecular and aggregate structures. The absorption spectra are dominated by π–π* transitions of the single molecules, whereas aggregation needs to be taken into account to obtain reasonable agreement between theory

  合成了一系列新的二氢四氮杂蒽酮和一种新的二氢四氮杂戊烷作为有机电子器件中使用的物质，并作为高级氮杂并氮烷的合适结构单元。芳族二胺与二氯二氰基吡嗪的缩合产生了这些三环/四环化合物。N的合成开发了预取代的苯二胺是为了在发色体系上引入多个官能团，例如酯，氨基或硝基。结构与光谱性质之间的关系可以通过紫外/可见吸收和荧光光谱以及分子和聚集体结构的DFT和TD-DFT计算得出。吸收光谱以单个分子的π–π *跃迁为主，而在某些情况下，需要考虑聚集以在理论和实验之间取得合理的一致性。进行了单晶X射线分析以检查其形态和固体堆积效应。最后，使用二氢四氮杂蒽并烷作为构建基，生成中离子八氮杂并五苯。
• Sane; Joshi, Journal of the Indian Chemical Society, 1932, vol. 9, p. 59,63
  作者：Sane、Joshi

  DOI：——

  日期：——
• An Improved Synthesis of<i>N</i>-Substituted-2-nitroanilines
  作者：S. M. S. Chauhan、Ram Singh、Geetanjali

  DOI：10.1081/scc-120022180

  日期：2003.1.8

  The reaction of 2-chloronitrobenzene with substituted amines/anilines in the presence of DBU (1,8-diazabicyclo[5.4.0]undec-7-ene) gives N-substituted-2-nitroanilines in good to excellent yields (>75-90%).