4-bromo-2-(((2-bromophenyl)amino)methyl)phenol | 1323851-44-0

• 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: 4-bromo-2-(((2-bromophenyl)amino)methyl)phenol
• 英文别名: 4-Bromo-2-[(2-bromoanilino)methyl]phenol
• CAS: 1323851-44-0
• 化学式: C₁₃H₁₁Br₂NO
• 分子量: 357.044
• InChiKey: YXYRGXROJBSKAP-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：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  32.3
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-bromo-2-(((2-bromophenyl)amino)methyl)phenol 、 异氰酸苯酯 以 氯仿 为溶剂， 以51%的产率得到1-(5-bromo-2-hydroxybenzyl)-1-(2-bromophenyl)-3-phenylurea
  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：

  5-溴水杨醛 在 sodium tetrahydroborate 作用下， 以 乙醇 为溶剂， 生成 4-bromo-2-(((2-bromophenyl)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

文献信息

• Synthesis, Characterization, Stability and Cytotoxic Evaluation of Novel Titanium(IV) Complexes of 8-Hydroxyquinoline and 2-Hydroxy-N-phenylbenzylamine Derivatives
  作者：Blassan Samuel、Madhvesh Pathak

  DOI：10.14233/ajchem.2020.22505

  日期：2020.2.10

  A new class of moisture stable heteroleptic titanium(IV) complexes, synthesized from 8-hydroxyquinoline of the type [(Q)2Ti(2-O-5-X-C6H3CH2NC6H4R] (3a-j), was prepared by reacting the antecedent molecule [(Q2)Ti(OiPr)2] (2) with various 2-hydroxy-N-phenyl-benzylamine analogues in 1:1 molar ratios in dry toluene (where, HQ = 8-hydroxyquinoline; iPr = isopropyl; R = H, 4-CH3, 4-OCH3, 2-Cl, 4-Cl, 2-Br, 4-Br; X= H, Br). Moisture sensitive study disclosed that these new metal complexes were unreacted for 72 h. Mass spectral data were employed for proving the mono-nuclearity of the new derivatives. Thermal decomposition pattern of the new derivatives was explained by thermogravimetric analyses. Elemental analyses data are in concordance with their expected values. The hexa-coordinated way of titanium-ligand linkage is further proved through NMR, FTIR, and UV-visible spectral studies. The cytotoxic efficiency of new complexes was tested against MDA-MB-231 human breast carcinoma cell line. Complex 3a exhibited the highest cytotoxic potential of 0.039 μM in comparison to all its analogues of this series by employing cisplatin as the standard

  一种新型的具有湿度稳定性的杂环钛（IV）配合物类别，由8-羟基喹啉[(Q)2Ti（2-O-5-X-C6H3CH2NC6H4R]（3a-j）合成，通过在干燥甲苯中以1:1摩尔比反应前体分子[(Q2)Ti（OiPr）2]（2）与各种2-羟基-N-苯基苄胺类似物（其中，HQ = 8-羟基喹啉; iPr = 异丙基; R = H，4-CH3，4-OCH3，2-Cl，4-Cl，2-Br，4-Br; X = H，Br）。湿度敏感性研究表明，这些新金属配合物在72小时内未反应。质谱数据用于证明新衍生物的单核性。通过热重分析解释了新衍生物的热分解模式。元素分析数据与预期值一致。通过NMR，FTIR和UV-Visible光谱研究进一步证明了钛-配体键合的六配位方式。测试了新配合物对MDA-MB-231人乳腺癌细胞系的细胞毒性效率。与所有同系列的类似物相比，3a复合物表现出最高的细胞毒性潜力（0.039μM），以顺铂为标准。
• 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.