4-bromo-2-(((4-chlorophenyl)imino)methyl)phenol | 16434-76-7

• 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-chlorophenyl)imino)methyl)phenol
• 英文别名: 4-Bromo-2-{[(4-chlorophenyl)imino]methyl}phenol；4-bromo-2-[(4-chlorophenyl)iminomethyl]phenol
• CAS: 16434-76-7
• 化学式: C₁₃H₉BrClNO
• 分子量: 310.578
• InChiKey: VSAVFQLPHIEAFP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 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：
  2

反应信息

• 作为反应物：
  描述：

  4-bromo-2-(((4-chlorophenyl)imino)methyl)phenol 在 sodium tetrahydroborate 作用下， 以 甲醇 、 二甲基亚砜 为溶剂， 反应 1.5h， 生成 6-bromo-3,4-dihydro-3-(4-chlorophenyl)-2H-benz[e]-1,3-oxazin-2-one
  参考文献：
  名称：

  A Quick Route for the Synthesis of 3-Aryl-3,4-dihydro-2H-benz[e]-1,3-oxazin-2-ones

  摘要：

  N-(2-羟基)-苄基-芳香胺（1）在20-25 ºC的DMSO中与碳酰二咪唑环化，20-30分钟后获得了3-芳基-3,4-二氢-2H-benz[e]-1,3-噁唑啉-2-酮（2），产率非常高。

  DOI：

  10.14233/ajchem.2013.14053
• 作为产物：
  描述：

  水杨醛 在 四氯化碳 、 乙醇 、 溴 作用下， 生成 4-bromo-2-(((4-chlorophenyl)imino)methyl)phenol
  参考文献：
  名称：

  Phototropic and Thermotropic Anils from 5-Bromosalicylaldehyde

  摘要：

  DOI：

  10.1021/ja01329a049

文献信息

• Vanadyl Binary Schiff Base Complexes Containing N₂O₂Coordination Sphere: Synthesis, Ab Initio Calculations and Thermodynamic Properties
  作者：Mozaffar Asadi、Mohammad Hadi Ghatee、Susan Torabi、Khosro Mohammadi、Fatemeh Moosavi

  DOI：10.5012/jkcs.2013.57.1.63

  日期：2013.2.20

  Some vanadyl complexes were synthesized by treating a methanolic solution of the appropriate Schiff base ligand and one equivalent of $VO(SO_4)_2$ to yield [($VOL_2^1-14}$)](L=Salicylaldehyde's derivatives, Schemes 1, 2). These oxovanadium (IV) complexes were characterized based on their FT-IR, UV-Vis spectroscopy and elemental analysis. The IR spectra suggest that coordination takes place through azomethine nitrogen and phenolate oxygen. In addition, the formation constants of the oxovanadium (IV) binary complexes were determined in methanolic medium. The ab initio calculations were also carried out to determine the structural and the geometrical properties of one of the complexes and its calculated vibrational frequencies were investigated.

  一些钒氧配合物是通过将适当的水杨醛衍生物希夫碱配体和等量的$VO(SO_4)_2$溶于甲醇溶液中合成的，生成[(VOL_2^1-14})](L=水杨醛衍生物，方案1、2)。这些四价氧化钒配合物根据其FT-IR、UV-Vis光谱和元素分析进行了表征。红外光谱表明配位通过偶氮甲碱氮和酚氧发生。此外，四价氧化钒二元配合物在甲醇介质中的形成常数也被测定。还进行了从头计算，以确定其中一个配合物的结构和几何性质及其计算的振动频率。
• 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
• Synthesis, characterization and molecular docking studies of phenoxyimine based ligands: Cytotoxicity, hemolytic activity and antioxidant assessment
  作者：Vinodkumar P. Sajjan、Lakkappa B. Anigol、Prabhuodeyara M. Gurubasavaraj、D. Kotresha、S.S. Pradhan、S. Venkatesh、Dhanashree Patil

  DOI：10.1016/j.molstruc.2022.133457

  日期：2022.10

  spectroscopic techniques. All compounds were screened for cytotoxicity activities against different cancer cell lines. Compound 3 exhibits significant cytotoxic activity with an IC50 value of 1.099 µM, 1.132 µM against COLO-205 (Colorectal adenocarcinoma) and A-549 (Lung carcinoma) cell line respectively, while compound 4 exhibits noteworthy cytotoxic activity with an IC50 value of 0.52 µM against MDA-MB-231(Breast

  采用摩尔比为1:1的不同取代水杨醛与苯胺一步反应缩合反应设计合成了一系列苯氧亚胺化合物。所有合成的化合物都通过分析和光谱技术进行了表征。筛选所有化合物对不同癌细胞系的细胞毒性活性。化合物3表现出显着的细胞毒活性，对 COLO-205（结肠直肠腺癌）和 A-549（肺癌）细胞系的 IC 50值分别为 1.099 μM、1.132 μM，而化合物4表现出显着的细胞毒活性，IC 50针对 MDA-MB-231（乳腺癌）的值为 0.52 µM。同样，其他化合物也表现出良好的细胞毒性特性。此外，苯氧亚胺化合物对 DPPH 自由基表现出最大的抗氧化活性。通过对 L929 正常细胞系的细胞相容性试验和对人红细胞的溶血试验证实了无毒活性。此外，所有化合物的计算机分子对接均针对 EGFR、HER-2 和 VEGF 进行。具有最小结合能ΔGb = -8.81 kcal/mol、ΔGb = -10.49 kcal/mol、ΔGb
• Mayadeo, M. S.; Nalgirkar, Jyoti V., Indian Journal of Chemistry, Section A: Inorganic, Physical, Theoretical and Analytical, 1988, vol. 27, # 5, p. 456 - 457
  作者：Mayadeo, M. S.、Nalgirkar, Jyoti V.

  DOI：——

  日期：——
• 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.