3-Amino-4-(4-fluoro-benzylamino)-benzoic acid methyl ester | 214903-44-3

• 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: 3-Amino-4-(4-fluoro-benzylamino)-benzoic acid methyl ester
• 英文别名: Methyl 3-amino-4-{[(4-fluorophenyl)methyl]amino}benzoate；methyl 3-amino-4-[(4-fluorophenyl)methylamino]benzoate
• CAS: 214903-44-3
• 化学式: C₁₅H₁₅FN₂O₂
• mdl: MFCD15006342
• 分子量: 274.295
• InChiKey: ZYTOFYOBFPHFRC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  64.4
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3-Amino-4-(4-fluoro-benzylamino)-benzoic acid methyl ester 在 溶剂黄146 、 N,N-二异丙基乙胺 、 lithium hydroxide 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 36.5h， 生成 1-(4-fluorobenzyl)-2-methyl-1H-benzimidazole-5-carboxylic acid
  参考文献：
  名称：

  Discovery of GSK1997132B a novel centrally penetrant benzimidazole PPARγ partial agonist

  摘要：

  The peroxisome proliferator-activated receptor gamma (PPAR gamma) is a ligand-activated nuclear receptor, thought to play a role in energy metabolism, glucose homeostasis and microglia-mediated neuroinflammation. A novel benzimidazole series of centrally penetrant PPAR gamma partial agonists has been identified. The optimization of PPAR gamma activity and in vivo pharmacokinetics leading to the identification of GSK1997132B a potent, metabolically stable and centrally penetrant PPAR gamma partial agonist, is described. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.06.088
• 作为产物：
  描述：

  4-氯-3-硝基苯甲酸甲酯 在 nickel dichloride 、 锌 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 12.0h， 生成 3-Amino-4-(4-fluoro-benzylamino)-benzoic acid methyl ester
  参考文献：
  名称：

  Synthesis of some new benzimidazolecarboxamides and evaluation of their antimicrobial activity

  摘要：

  A series of 1,2-disubstituted benzimidazole-5(6)-carboxamides was prepared and evaluated in vitro for antimicrobial activity against Staphyloccus aureus, Escherichia coli and Candida albicans. The precursor benzimidazolecarboxylic acids 4a-c and 9a-c were prepared via oxidative condensation of diaminobenzoic acids with aldehydes and via several steps over the 2(1H)-benzimidazolones, respectively. All acids were converted to their acyl chlorides with SOCI2, then amidified with several N,N'-dialkylaminoethyl derivatives. Compounds 8a-c, 20 and 22 exhibited the best activity. (C) 1998 Elsevier Science S.A. All rights reserved.

  DOI：

  10.1016/s0014-827x(98)00045-7

文献信息

• Synthesis and biological evaluation of quinoxaline derivatives as tubulin polymerization inhibitors that elevate intracellular <scp>ROS</scp> and triggers apoptosis via mitochondrial pathway
  作者：Jianguo Qi、Jing Huang、Xiaomin Zhou、Wen Luo、Jiaxin Xie、Linqiang Niu、Zhijie Yan、Yang Luo、Yuhui Men、Yanan Chen、Yahong Zhang、Jianhong Wang

  DOI：10.1111/cbdd.13459

  日期：2019.4

  antiproliferative activity with IC50 in the range of 0.19-0.51 μM. The compound inhibited tubulin polymerization and disrupted the microtubule network, leading to G2/M phase arrest. Furthermore, compound 12 induced ROS production and malfunction of mitochondrial membrane potential. Compound 12 led to cancer cells apoptosis in a dose-dependent manner. Western blot analysis showed that compound 12 induced up-regulation

  合成了一系列新颖的喹喔啉衍生物，并评估了它们在三种人类癌细胞系中的抗增殖活性。化合物12表现出最有效的抗增殖活性，IC50在0.19-0.51μM的范围内。该化合物抑制微管蛋白聚合并破坏微管网络，导致G2 / M期停滞。此外，化合物12诱导了ROS的产生和线粒体膜电位的故障。化合物12以剂量依赖性方式导致癌细胞凋亡。蛋白质印迹分析表明，化合物12诱导p21的上调并影响细胞周期相关蛋白的表达。结合模式也通过分子对接来探测。