ethyl 2-(4-(dimethylamino)phenyl)-1H-benzo[d]imidazole-5-carboxylate

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并咪唑类
• 英文名称: ethyl 2-(4-(dimethylamino)phenyl)-1H-benzo[d]imidazole-5-carboxylate
• 英文别名: 2-(4-dimethylaminophenyl)-1H-benzoimidazole-5-carboxylic acid ethyl ester；ethyl 2-(4-dimethylaminophenyl)-1H-benzimidazole-5-carboxylate；ethyl 2-[4-(dimethylamino)phenyl]-3H-benzimidazole-5-carboxylate
• 化学式: C₁₈H₁₉N₃O₂
• 分子量: 309.368
• InChiKey: ZPBDYWBATZCPHK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  58.2
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  ethyl 2-(4-(dimethylamino)phenyl)-1H-benzo[d]imidazole-5-carboxylate 在 lithium hydroxide monohydrate 、 水 作用下， 以 四氢呋喃 为溶剂， 以99%的产率得到2-(4-二甲基氨基苯基)-1H-苯并咪唑-5-羧酸
  参考文献：
  名称：

  WO2018054989A5

  摘要：

  公开号：

  WO2018054989A5
• 作为产物：
  描述：

  4-氨基-3-硝基苯甲酸乙酯 在 palladium 10% on activated carbon 、 甲酸铵 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 生成 ethyl 2-(4-(dimethylamino)phenyl)-1H-benzo[d]imidazole-5-carboxylate
  参考文献：
  名称：

  Synthesis and evaluation of antimycobacterial activity of new benzimidazole aminoesters

  摘要：

  A total of 51 novel benzimidazoles were synthesized by a 4-step reaction starting from basic compound 4-fluoro-3-nitrobenzoic acid under relatively mild reaction conditions. The structure of the novel benzimidazoles was confirmed by mass spectra as well as H-1 NMR spectroscopic data. Out of the 51 novel synthesized compounds, 42 of them were screened for their antimycobacterial activity against Mycobacterium tuberculosis H(37)Rv strain using BacTiter-Glo (TM) Microbial Cell Viability (BTG) method. Results of activity screened using Alamar Blue method was also provided for comparison purposes. Two of the novel benzimidazoles synthesized showed moderately good activity with 1050 of less than 15 mu M. Compound 5g, ethyl 2-(4-(trifluoromethyl)phenyl)-1-(2-morpholinoethyl)-1H-benzo[d]imidazole-5-carboxylate, was found to be the most active with IC50 of 11.52 mu M. (C) 2014 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.06.025

文献信息

• Discovery of a potent and highly fluorescent sirtuin inhibitor
  作者：Y. K. Yoon、M. A. Ali、A. C. Wei、T. S. Choon、A. N. Shirazi、K. Parang

  DOI：10.1039/c5md00307e

  日期：——

  Highly fluorescent sirtuin inhibitor was discovered to possess growth inhibitory effect against multiple cancer cell lines.

  一种高度荧光的去乙酰化酶抑制剂被发现对多种癌细胞系具有生长抑制作用。
• Benzoimidazole derivatives as anticancer agents
  申请人：CENTRE LEON BERARD

  公开号：US11384081B2

  公开（公告）日：2022-07-12

  The disclosure relates to benzoimidazole derivatives, acting as anticancer drugs, as well as pharmaceutical composition containing said compounds. These compounds are able to firstly inhibit the protein/protein interactions of the MAP Kinase Erk, leading to inhibition of proliferation and secondly to induce apoptosis in human cancer cell lines.

  本公开涉及作为抗癌药物的苯并咪唑衍生物，以及含有上述化合物的药物组合物。这些化合物首先能抑制 MAP 激酶 Erk 的蛋白/蛋白相互作用，从而抑制增殖，其次能诱导人类癌细胞株凋亡。
• BENZOIMIDAZOLE DERIVATIVES AS ANTICANCER AGENTS
  申请人：Centre Leon Berard

  公开号：EP3515904A1

  公开（公告）日：2019-07-31
• Benzoimidazole Derivatives As Anticancer Agents
  申请人：CENTRE LEON BERARD

  公开号：US20220348587A1

  公开（公告）日：2022-11-03

  The disclosure relates to benzoimidazole derivatives, acting as anticancer drugs, as well as pharmaceutical composition containing the compounds. These compounds are able to firstly inhibit the protein/protein interactions of the MAP Kinase Erk, leading to inhibition of proliferation and secondly to induce apoptosis in human cancer cell lines.
• [EN] BENZOIMIDAZOLE DERIVATIVES AS ANTICANCER AGENTS<br/>[FR] DÉRIVÉS DE BENZOIMIDAZOLE EN TANT QU'AGENTS ANTICANCÉREUX
  申请人：CENTRE LEON BERARD

  公开号：WO2018054989A1

  公开（公告）日：2018-03-29

  The invention relates to benzoimidazole derivatives, acting as anticancer drugs, as well as pharmaceutical composition containing said compounds. These compounds are able to firstly inhibit the protein/protein interactions of the MAP Kinase Erk, leading to inhibition of proliferation and secondly to induce apoptosis in human cancer cell lines.