3-氨基-4-苯基氨基苯甲酸甲酯 | 514206-06-5

• 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-氨基-4-苯基氨基苯甲酸甲酯
• 中文别名: 甲基3-氨基-4-(苯基氨基)苯酸盐
• 英文名称: 3-amino-4-phenylaminobenzoic acid methyl ester
• 英文别名: methyl 3-amino-4-(phenylamino)benzoate；3-amino-4-anilino-benzoic acid methyl ester；3-Amino-4-anilino-benzoesaeure-methylester；methyl 3-amino-4-anilinobenzoate
• CAS: 514206-06-5
• 化学式: C₁₄H₁₄N₂O₂
• 分子量: 242.277
• InChiKey: XWRIEMIJMFMCPC-UHFFFAOYSA-N

物化性质

• 熔点：
  101-103 °C
• 沸点：
  412.5±35.0 °C(Predicted)
• 密度：
  1.238±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 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：
  64.4
• 氢给体数：
  2
• 氢受体数：
  4

安全信息

• 储存条件：
  应存于室温、密封且干燥的环境。

反应信息

• 作为反应物：
  描述：

  3-氨基-4-苯基氨基苯甲酸甲酯 在 manganese(IV) oxide 、 氯化锆(IV) 作用下， 以 乙醇 为溶剂， 反应 0.58h， 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 palladium on activated charcoal N-甲基吗啉 、 盐酸 、 氢气 、 铜 作用下， 以 甲醇 、 异戊醇 、 乙酸乙酯 为溶剂， 反应 36.0h， 生成 3-氨基-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

• [EN] OXADIAZOLE DERIVATIVES AND THEIR USE AS NICOTINIC ACETYLCHOLINE RECEPTOR MODULATORS<br/>[FR] DÉRIVÉS D'OXADIAZOLE ET LEUR UTILISATION COMME MODULATEURS DES RÉCEPTEURS NICOTINIQUES DE L'ACÉTYLCHOLINE
  申请人：GLAXO GROUP LTD

  公开号：WO2009071577A1

  公开（公告）日：2009-06-11

  Oxadiazole derivatives of formula (I) where ring A is a bicyclic or tricyclic system. Claimed compounds are active on nicotinic acetylcholine receptors (nAChRs), and are useful to treat neurological, psychiatric, and gastrointestinal disorders, as well as sepsis and obesity.

  Oxadiazole衍生物的化学式（I），其中环A是一个双环或三环系统。所述化合物对尼古丁型乙酰胆碱受体（nAChRs）具有活性，并可用于治疗神经系统、精神病学和胃肠道疾病，以及败血症和肥胖症。
• 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。
• [EN] HEPATITIS B CORE PROTEIN MODULATORS<br/>[FR] MODULATEURS DES PROTÉINES DU NOYAU DE L'HÉPATITE B
  申请人：ASSEMBLY BIOSCIENCES INC

  公开号：WO2017048954A1

  公开（公告）日：2017-03-23

  The present disclosure provides, in part, compounds having allosteric effector properties against Hepatitis B virus Cp. Also provided herein are methods of treating viral infections, such as hepatitis B, comprising administering to a patient in need thereof a disclosed compound.

  本公开提供了部分具有对乙型肝炎病毒Cp的变构效应物质。本文还提供了治疗病毒感染（如乙型肝炎）的方法，包括向需要的患者施用所述化合物。
• 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。
• THERAPEUTIC DRUG FOR LIPID-PEROXIDATION-INDUCED DISEASES AND SCREENING METHOD FOR THERAPEUTIC DRUGS FOR LIPID-PEROXIDATION-INDUCED DISEASES
  申请人：Yamada, Ken-Ichi

  公开号：EP3650860A1

  公开（公告）日：2020-05-13

  The present invention provides: an assay method that uses a compound represented by formula (I) as a fluorescent probe molecule and that is for detecting the lipid peroxidation suppression activity of a test compound; an assay kit that uses the assay method; a screening method that uses the assay method; and a pharmaceutical composition that is for the treatment, etc. of diseases (such as age-related macular degeneration) that are induced by lipid peroxidation reactions.

  本发明提供了：一种使用式（I）代表的化合物作为荧光探针分子的检测方法，该方法用于检测受试化合物的脂质过氧化抑制活性；一种使用该检测方法的检测试剂盒；一种使用该检测方法的筛选方法；以及一种药物组合物，该药物组合物用于治疗由脂质过氧化反应诱发的疾病（如老年性黄斑变性）等。