4-甲氧基-2-(苯基氨基)苯甲酸 | 19218-83-8

• 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: 4-甲氧基-2-(苯基氨基)苯甲酸
• 英文名称: 5-methoxydiphenylamine-2-carboxylic acid
• 英文别名: 4-methoxy-2-(phenylamino)benzoic acid；2-anilino-4-methoxy-benzoic acid；2-Anilino-4-methoxy-benzoesaeure；5-Methoxy-diphenylamin-carbonsaeure-(2)；2-Anilino-anissaeure；2-anilino-4-methoxybenzoic acid
• CAS: 19218-83-8
• 化学式: C₁₄H₁₃NO₃
• 分子量: 243.262
• InChiKey: MFKNPBLMWQGRDT-UHFFFAOYSA-N

物化性质

• 熔点：
  178 °C
• 沸点：
  399.5±32.0 °C(Predicted)
• 密度：
  1.266±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  18
• 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：
  58.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-甲氧基-2-(苯基氨基)苯甲酸 在 三氯氧磷 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 9-氯-3-甲氧基吖啶
  参考文献：
  名称：

  Design, synthesis and evaluation of acridine derivatives as multi-target Src and MEK kinase inhibitors for anti-tumor treatment

  摘要：

  Clinical studies have shown enhanced anticancer effects of combined inhibition of Src and MEK kinases. Development of multi-target drugs against Src and MEK is of potential therapeutic advantage against cancers. As a follow-up of our previous studies, and by using molecular docking method, we designed and synthesized a new series of 9-anilinoacridines containing phenyl-urea moieties as potential novel dual Src and MEK inhibitors. The anti-proliferative assays against K562 and HepG-2 tumor cells showed that most of the derivatives displayed good cytotoxicity in vitro. In particular, kinase inhibition assays showed that compound 8m inhibited Src (59.67%) and MEK (43.23%) at 10 mu M, and displayed moderate inhibitory activity against ERK and AKT, the downstream effectors of both Src and MEK. Moreover, compound 8m was found to induce K562 cells apoptosis. Structure-activity relationships of these derivatives were analyzed. Our study suggested that acridine scaffold, particularly compound 8m, is of potential interest for developing novel multi-target Src and MEK kinase inhibitors. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2015.12.011
• 作为产物：
  描述：

  4-甲氧基-2-硝基苯甲酸 在 甲醇 、 镍 、 铜 、 potassium carbonate 、 copper(l) chloride 作用下， 生成 4-甲氧基-2-(苯基氨基)苯甲酸
  参考文献：
  名称：

  Brockmann et al., Chemische Berichte, 1956, vol. 89, p. 2174,2178

  摘要：

  DOI：

文献信息

• FACILE OXIDATION OF ALCOHOLS BY 3-HYDROXY-<i>N</i>-METHYLACRIDINIUM ION (A NEW NAD⁺MODEL COMPOUND)
  作者：Seiji Shinkai、Hisatake Hamada、Hideo Kuroda、Osamu Manabe

  DOI：10.1246/cl.1980.1235

  日期：1980.10.5

  3-Hydroxy-N-methylacridinium iodide (Ac+OH) oxidized alcohols with the aid of potassium t-butoxide, whereas N-methylacridinium iodide (Ac+) could not oxidize alcohols under the same reaction conditions. The results indicate that the 3-hydroxyl group is crucial in modifying an N-methylacridinium nucleus as an NAD+ model oxidizing agent.

  3-Hydroxy-N-methylacridinium iodide (Ac+OH) 在叔丁醇钾的帮助下氧化醇，而 N-methylacridinium iodide (Ac+) 在相同的反应条件下不能氧化醇。结果表明，3-羟基对于将 N-甲基吖啶核修饰为 NAD+ 模型氧化剂至关重要。
• Synthesis of Tribenzo[<i>b</i>,<i>d</i>,<i>f</i>]azepines via Cascade π-Extended Decarboxylative Annulation Involving Cyclic Diaryliodonium Salts
  作者：Tao Hu、Zenghui Ye、Kai Zhu、Kai Xu、Yanqi Wu、Fengzhi Zhang

  DOI：10.1021/acs.orglett.9b04269

  日期：2020.1.17

  step-economical protocol is that the carboxylic acid functionality was employed as both a traceless directing group for the N-H activation/arylation and a functional handle for the tandem π-extended decarboxylative annulation.

  在Pd（II）催化下，以易得的2-氨基苯甲酸和环状高价二芳基碘鎓试剂为起始原料，可以有效地制备各种官能化的三苯并[b，d，f] pine子。这种经济实惠的步骤的关键在于，羧酸官能团既用作NH活化/芳基化的无痕导向基团，又用作串联π扩展的脱羧环化的官能团。
• [EN] QUINAZOLINE POTASSIUM CHANNEL INHIBITORS<br/>[FR] INHIBITEURS DU CANAL POTASSIQUE A BASE DE QUINAZOLINE
  申请人：MERCK & CO INC

  公开号：WO2005030217A1

  公开（公告）日：2005-04-07

  The present invention relates to compounds having the structure (I) useful as potassium channel inhibitors to treat cardiac arrhythmias, and the like.

  本发明涉及具有结构（I）的化合物，可用作钾通道抑制剂，用于治疗心律失常等。
• Quinazoline potassium channel inhibitors
  申请人：Trotter Wesley B.

  公开号：US20070054894A1

  公开（公告）日：2007-03-08

  The present invention relates to compounds having the structure (I) useful as potassium channel inhibitors to treat cardiac arrhythmias, and the like.

  本发明涉及具有结构（I）的化合物，用于作为钾通道抑制剂治疗心律失常等。
• MATRIX FOR MALDI MASS SPECTROMETRY AND MALDIMASS SPECTROMETRY METHOD
  申请人：Shindo Mitsuru

  公开号：US20140151548A1

  公开（公告）日：2014-06-05

  Provided is a matrix for MALDI mass spectrometry that has a high ability of ionizing low-molecular-weight compounds, and makes it possible to make measurement in a negative ion mode. The matrix is a matrix for mass spectrometry that contains one or more compounds selected from the group consisting of compounds each represented by the following general formula (I), (II) or (III), and their salts thereof. In the formulae (I), (II) and (III), X and Z are each C or N; R 1 and R 5 are each selected from the group consisting of H, an alkyl group, a (substituted) aryl group, a (substituted) arylalkyl group, and a (substituted) heteroaryl group; R 2 and R 6 are each selected from the group consisting of H, an alkyl group, an alkoxyl group, an amino group, a halogen atom, a nitro group, an allyl group, a (substituted) aryl group, and a (substituted) heteroaryl group; and R 7 and R 8 are each selected from the group consisting of H and an amino group provided that a case where R 1 =R 2 =H, and a case where R 7 =R 8 =an amino group are excluded.

  提供的是一种用于MALDI质谱的矩阵，具有高能力电离低分子量化合物的能力，并使得在负离子模式下进行测量成为可能。该矩阵是一种质谱矩阵，包含从由以下通式（I）、（II）或（III）表示的化合物组成的化合物中选择的一个或多个化合物及其盐。在式（I）、（II）和（III）中，X和Z分别为C或N；R1和R5分别选择自H、烷基、（取代）芳基、（取代）芳基烷基和（取代）杂芳基组成的群；R2和R6分别选择自H、烷基、烷氧基、氨基、卤素原子、硝基、烯丙基、（取代）芳基和（取代）杂芳基组成的群；R7和R8分别选择自H和氨基，但排除R1=R2=H和R7=R8=氨基的情况。