methyl 4-[(2-methyl-5-nitrophenylamino)methyl]benzoate | 1202748-41-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: methyl 4-[(2-methyl-5-nitrophenylamino)methyl]benzoate
• 英文别名: Methyl 4-[(2-methyl-5-nitrophenylamino)meth-yl]benzoate；methyl 4-[(2-methyl-5-nitroanilino)methyl]benzoate
• CAS: 1202748-41-1
• 化学式: C₁₆H₁₆N₂O₄
• 分子量: 300.314
• InChiKey: BFTQIEFJBFPZGJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.19
• 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：

  methyl 4-[(2-methyl-5-nitrophenylamino)methyl]benzoate 在 一水合肼 作用下， 以 水 为溶剂， 以83%的产率得到methyl 4-[(5-amino-2-methylphenylamino)methyl]benzoate
  参考文献：
  名称：

  Reductive transformations of Schiff bases in the synthesis of functionally substituted heteroaromatic amines

  摘要：

  Schiff bases synthesized by condensation of 5- and 6-aminoquinolines, 5-amino-2-methylquinoline, nitroanilines, and pyrimidinylaminoanilines with substituted benzaldehydes and pyridinecarbaldehydes were reduced with sodium tetrahydridoborate in acetic acid to obtain the corresponding N-aryl(hetaryl)benzylamines, N-(pyridylmethyl)anilines, and N-(1,2,3,4-tetrahydroquinolyl)benzylamine derivatives. The reduction of arylhetarylimines with hydrazine hydrate in the presence of Raney nickel involved only the azomethine C=N bond, while the nitrogen-containing heteroaromatic ring remained intact. Under analogous conditions, nitrosubstituted Schiff bases and benzyl- and pyridylmethylamines were converted into previously unknown N-(aminobenzyl)quinolinamines and aryl(pyridyl)methyl-substituted phenylenediamines.

  DOI：

  10.1134/s1070428009070148
• 作为产物：
  描述：

  2-氨基-4-硝基甲苯 在 sodium tetrahydroborate 、 硼酸 作用下， 以 乙醇 、 苯 为溶剂， 生成 methyl 4-[(2-methyl-5-nitrophenylamino)methyl]benzoate
  参考文献：
  名称：

  还原反应中功能性取代的席夫碱

  摘要：

  在硼氢化钠与酸性活化剂，水合肼在阮内镍，阮内合金存在下的反应中，研究了硝基苯胺，嘧啶基氨基苯胺，5-氨基喹啉，5-氨基喹喔啉衍生物与4-甲基甲酰基苯甲酸酯缩合得到的功能取代的席夫碱。氢氧化钾的存在。通过偶氮甲胺的还原，获得了苯胺，喹啉胺，芳基氨基嘧啶和苯二胺的新苄基衍生物。

  DOI：

  10.1134/s1070428013020073

文献信息

• Synthesis, Biological Activities and Docking Studies of Novel 4-(Arylaminomethyl)benzamide Derivatives as Potential Tyrosine Kinase Inhibitors
  作者：Elena Kalinichenko、Aliaksandr Faryna、Viktoria Kondrateva、Alena Vlasova、Valentina Shevchenko、Alla Melnik、Olga Avdoshko、Alla Belko

  DOI：10.3390/molecules24193543

  日期：——

  number of new compounds containing the 4-(aminomethyl)benzamide fragment as a linker were designed and synthesized, and their biological activities were evaluated as potential anticancer agents. The cytotoxicity activity of the designed compounds was studied in two hematological and five solid cell lines in comparison with the reference drugs. Targeted structures against eight receptor tyrosine kinases

  设计并合成了许多含有4-(氨基甲基)苯甲酰胺片段作为接头的新化合物，并评估了它们的生物活性作为潜在的抗癌剂。与参考药物相比，在两种血液学和五种固体细胞系中研究了设计化合物的细胞毒性活性。研究了针对八种受体酪氨酸激酶的靶向结构，包括 EGFR、HER-2、HER-4、IGF1R、InsR、KDR、PDGFRa 和 PDGFRb。大多数化合物对测试的激酶显示出有效的抑制活性。在分子的酰胺或胺部分中具有（三氟甲基）苯环的类似物 11 和 13 被证明对 EGFR 具有高度效力，在 10 nM 时分别具有 91% 和 92% 的抑制作用。对蛋白质数据库 (PDB) 数据库中包含的九种蛋白激酶的合成目标化合物进行对接。类似物 10 的分子建模结果表明，使用 4-（氨基甲基）苯甲酰胺作为灵活的接头导致分子的整体几何形状有利，这允许绕过大量异亮氨酸残基并提供与活性分子的必要结合。 T315I 突变体 Abl
• Synthesis of N-aryl benzamides containing pharmacophoric tyrosine kinase inhibitor fragments
  作者：E. V. Koroleva、Zh. V. Ignatovich、K. N. Gusak、A. L. Ermolinskaya、Yu. V. Sinyutich

  DOI：10.1134/s1070428015010182

  日期：2015.1

  New N-aryl 4-(arylaminomethyl)benzamides containing pharmacophoric heterocyclic fragments have been synthesized from 2-arylaminopyrimidine, 1-methylpiperazine, and morpholine derivatives and substituted benzoic acids.
• Preparative synthesis of heterocyclic and aromatic N-benzyl amines
  作者：E. V. Koroleva、K. N. Gusak、A. L. Ermolinskaya、Zh. V. Ignatovich

  DOI：10.1134/s107042801304012x

  日期：2013.4

  A simple and highly efficient procedure has been proposed for the synthesis of heterocyclic and aromatic N-benzyl amines via reductive amination of substituted aromatic aldehydes in the presence of sodium tetrahydridoborate-acetic acid system generating reactive sodium triacetoxyhydridoborate.