4-bromo-2-[(4-fluorophenylimino)methyl]phenol | 316131-19-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 4-bromo-2-[(4-fluorophenylimino)methyl]phenol
• 英文别名: 4-bromo-2-{(E)-[(4-fluorophenyl)imino]methyl}phenol；4-bromo-2-[(4-fluorophenyl)iminomethyl]phenol
• CAS: 316131-19-8
• 化学式: C₁₃H₉BrFNO
• 分子量: 294.123
• InChiKey: GSSURLNEDJAYKV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  32.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-bromo-2-[(4-fluorophenylimino)methyl]phenol 在 sodium tetrahydroborate 作用下， 以 乙醇 为溶剂， 以82%的产率得到4-bromo-2-(((4-fluorophenyl)amino)methyl)phenol
  参考文献：
  名称：

  Design, synthesis and biological evaluation of urea derivatives from o-hydroxybenzylamines and phenylisocyanate as potential FabH inhibitors

  摘要：

  FabH, beta-ketoacyl-acyl carrier protein (ACP) synthase III, is a particularly attractive target, since it is central to the initiation of fatty acid biosynthesis and is highly conserved among Gram-positive and Gram-negative bacteria. A series of o-hydroxybenzylamines 1-16 and its corresponding new urea derivatives 17-32 were synthesized and fully characterized by spectroscopic methods and elemental analysis. This new urea derivatives class demonstrates strong antibacterial activity. Escherichia coli FabH inhibitory assay and docking simulation indicated that the compounds 1-(5-bromo-2-hydroxybenzyl)-1-(4-fluorophenyl)-3-phenylurea (18) and 1-(5-bromo-2-hydroxybenzyl)-1-(4-chlorophenyl)-3-phenylurea (20) were potent inhibitors of E. coli FabH. Crown Copyright (C) 2011 Published by Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.06.049
• 作为产物：
  描述：

  4-氟苯胺 、 5-溴水杨醛 以 乙醇 为溶剂， 反应 5.0h， 生成 4-bromo-2-[(4-fluorophenylimino)methyl]phenol
  参考文献：
  名称：

  卤化双齿N，O供体席夫碱配体的新型铜（II）和锌（II）配合物：合成，表征，晶体结构，DNA结合，分子对接，DFT和TD-DFT计算研究

  摘要：

  摘要八个新颖的配合物，包括：[Cu（L1）2]：C1，[Cu（L2）2]：C2，[Cu（L3）2]：C3，[Cu（L4）2]：C4，[Zn（ L1）2]：Z1，[Zn（L2）2]：Z2，[Zn（L3）2]：Z3和[Zn（L4）2]：Z4，带有四个双齿N，O-施主卤代双席夫碱性配体（HL1：4-溴-2-[（4-氟苯基亚氨基）甲基]苯酚; HL2：4-溴-2-[（4-氯苯基亚氨基）甲基]苯酚; HL3：4-溴-2-[[4 -溴苯基亚氨基）甲基]苯酚；合成了HL4：4-溴-2-[（4-碘苯基亚氨基）甲基]苯酚），并通过SC-XRD，FT-IR，UV-Vis和1H NMR光谱技术证实了它们的结构。单晶X射线衍射分析表明，在锌络合物中形成了扭曲的四面体几何形状，而在C3和C4的铜（II）络合物中都形成了略微扭曲的正方形平面几何形状。使用Def2-TZVP基集，使用B3LYP方法通过DFT和TD-DF

  DOI：

  10.1016/j.ica.2020.120004

文献信息

• Design, synthesis and biological evaluation of urea derivatives from o-hydroxybenzylamines and phenylisocyanate as potential FabH inhibitors
  作者：Zi-Lin Li、Qing-Shan Li、Hong-Jia Zhang、Yang Hu、Di-Di Zhu、Hai-Liang Zhu

  DOI：10.1016/j.bmc.2011.06.049

  日期：2011.8

  FabH, beta-ketoacyl-acyl carrier protein (ACP) synthase III, is a particularly attractive target, since it is central to the initiation of fatty acid biosynthesis and is highly conserved among Gram-positive and Gram-negative bacteria. A series of o-hydroxybenzylamines 1-16 and its corresponding new urea derivatives 17-32 were synthesized and fully characterized by spectroscopic methods and elemental analysis. This new urea derivatives class demonstrates strong antibacterial activity. Escherichia coli FabH inhibitory assay and docking simulation indicated that the compounds 1-(5-bromo-2-hydroxybenzyl)-1-(4-fluorophenyl)-3-phenylurea (18) and 1-(5-bromo-2-hydroxybenzyl)-1-(4-chlorophenyl)-3-phenylurea (20) were potent inhibitors of E. coli FabH. Crown Copyright (C) 2011 Published by Elsevier Ltd. All rights reserved.
• Novel copper(II) and zinc(II) complexes of halogenated bidentate N,O-donor Schiff base ligands: Synthesis, characterization, crystal structures, DNA binding, molecular docking, DFT and TD-DFT computational studies
  作者：Hadi Kargar、Reza Behjatmanesh-Ardakani、Vajiheh Torabi、Asiyehalsadat Sarvian、Zahra Kazemi、Zahra Chavoshpour-Natanzi、Valiollah Mirkhani、Atefeh Sahraei、Muhammad Nawaz Tahir、Muhammad Ashfaq

  DOI：10.1016/j.ica.2020.120004

  日期：2021.1

  bidentate N,O-donor halogenated bis-Schiff base ligands (HL1: 4-Bromo-2-[(4-fluorophenylimino) methyl]phenol; HL2: 4-Bromo-2-[(4-chlorophenylimino)methyl]phenol; HL3: 4-Bromo-2-[(4-bromophenylimino) methyl]phenol; HL4: 4-Bromo-2-[(4- iodophenylimino)methyl]phenol) were synthesized and their structures were proved by SC-XRD, FT-IR, UV-Vis, and 1H NMR spectroscopic techniques. The single crystal X-ray diffraction

  摘要八个新颖的配合物，包括：[Cu（L1）2]：C1，[Cu（L2）2]：C2，[Cu（L3）2]：C3，[Cu（L4）2]：C4，[Zn（ L1）2]：Z1，[Zn（L2）2]：Z2，[Zn（L3）2]：Z3和[Zn（L4）2]：Z4，带有四个双齿N，O-施主卤代双席夫碱性配体（HL1：4-溴-2-[（4-氟苯基亚氨基）甲基]苯酚; HL2：4-溴-2-[（4-氯苯基亚氨基）甲基]苯酚; HL3：4-溴-2-[[4 -溴苯基亚氨基）甲基]苯酚；合成了HL4：4-溴-2-[（4-碘苯基亚氨基）甲基]苯酚），并通过SC-XRD，FT-IR，UV-Vis和1H NMR光谱技术证实了它们的结构。单晶X射线衍射分析表明，在锌络合物中形成了扭曲的四面体几何形状，而在C3和C4的铜（II）络合物中都形成了略微扭曲的正方形平面几何形状。使用Def2-TZVP基集，使用B3LYP方法通过DFT和TD-DF