2,4‐dibromo‐6‐[(4‐fluorobenzylimino)methyl]phenol | 477848-41-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 2,4‐dibromo‐6‐[(4‐fluorobenzylimino)methyl]phenol
• 英文别名: 2,4-Dibromo-6-{[(4-fluorobenzyl)imino]methyl}benzenol；2,4-dibromo-6-[(4-fluorophenyl)methyliminomethyl]phenol
• CAS: 477848-41-2
• 化学式: C₁₄H₁₀Br₂FNO
• 分子量: 387.046
• InChiKey: RHOVHTSGPYTOHP-UHFFFAOYSA-N

物化性质

• 沸点：
  416.3±45.0 °C(Predicted)
• 密度：
  1.67±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 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：

  2,4‐dibromo‐6‐[(4‐fluorobenzylimino)methyl]phenol 在 sodium tetrahydroborate 作用下， 以 乙醇 为溶剂， 以78%的产率得到2,4-dibromo-6-((4-fluorobenzylamino)methyl)phenol
  参考文献：
  名称：

  Synthesis and structure–activity relationships of N-benzyl-N-(X-2-hydroxybenzyl)-N′-phenylureas and thioureas as antitumor agents

  摘要：

  Two series of novel N-benzyl-N-(X-2-hydroxybenzyl)-N'-phenylureas and thioureas (1a-18a; 1b-18b) as potential EGFR and HER-2 kinase inhibitors have been discovered. These compounds displayed good EGFR and HER-2 inhibitory activity and the SARs are also been studied. Especially compound 7b demonstrated significant EGFR and HER-2 inhibitory activity (IC50 = 0.08 mu M for EGFR and IC50 = 0.35 mu M for HER-2). Docking simulation was performed to position compound 7b into the EGFR active site to determine the probable binding conformation and antiproliferative assay results indicating that these series of urea and thioureas own high antiproliferative activity against MCF-7. Above all, thiourea 7b would be a potential anticancer agent deserves further research. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2009.10.054
• 作为产物：
  描述：

  3,5-二溴水杨醛 、 对氟苄胺 以 乙醇 为溶剂， 生成 2,4‐dibromo‐6‐[(4‐fluorobenzylimino)methyl]phenol
  参考文献：
  名称：

  Synthesis and structure–activity relationships of N-benzyl-N-(X-2-hydroxybenzyl)-N′-phenylureas and thioureas as antitumor agents

  摘要：

  Two series of novel N-benzyl-N-(X-2-hydroxybenzyl)-N'-phenylureas and thioureas (1a-18a; 1b-18b) as potential EGFR and HER-2 kinase inhibitors have been discovered. These compounds displayed good EGFR and HER-2 inhibitory activity and the SARs are also been studied. Especially compound 7b demonstrated significant EGFR and HER-2 inhibitory activity (IC50 = 0.08 mu M for EGFR and IC50 = 0.35 mu M for HER-2). Docking simulation was performed to position compound 7b into the EGFR active site to determine the probable binding conformation and antiproliferative assay results indicating that these series of urea and thioureas own high antiproliferative activity against MCF-7. Above all, thiourea 7b would be a potential anticancer agent deserves further research. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2009.10.054

文献信息

• Some divalent metal(II) complexes of salicylaldehyde-derived Schiff bases: Synthesis, spectroscopic characterization, antimicrobial and <i>in vitro</i> anticancer studies
  作者：J. Devi、M. Yadav、D. Kumar、L.S. Naik、D.K. Jindal

  DOI：10.1002/aoc.4693

  日期：2019.2

  been synthesized from uninegative Schiff base ligands (HL1–HL4) designed by condensation of 4‐fluorobenzylamine with 2‐hydroxy‐1‐naphthaldehyde/3,5‐dichlorosalicylaldehyde/3,5‐dibromosalicylaldehyde/3‐bromo‐5‐chlorosalicylaldehyde. The compounds were successfully characterized using spectroscopic and physiochemical methods together with elemental analysis. Spectroscopic elucidation indicates a monobasic

  单核过渡金属（II）的种类M（L）的配合物2 ⋅2H 2 O（其中M =钴，镍，铜，锌）已经从uninegative席夫碱配体合成（HL 1 -HL 4）通过缩合设计4-氟苄胺与2-羟基-1-萘醛/ 3,5-二氯水杨醛/ 3,5-二溴水杨醛/ 3-溴-5-氯水杨醛。使用光谱和物理化学方法以及元素分析已成功表征了这些化合物。光谱分析表明配体的一元二齿性质是通过去质子化的酚氧和偶氮甲碱氮原子配位的，这表明中心金属离子周围是八面体的几何形状。筛选配合物和配体的对细菌和真菌菌株的体外抗微生物活性，锌（II）配合物对被测微生物菌株更具活性。此外，由于螯合过程，发现金属络合物比未络合的配体具有更高的活性，此外，与细菌菌株相比，该络合物对真菌菌株的活性更高。使用MTT比色法评估了所有化合物对人肺泡腺癌上皮细胞系（A549），人乳腺腺癌细胞系（MCF7），人前列腺癌细胞系（DU145）和一种正常人肺细胞系
• Synthesis and structure–activity relationships of N-benzyl-N-(X-2-hydroxybenzyl)-N′-phenylureas and thioureas as antitumor agents
  作者：Huan-Qiu Li、Tao Yan、Ying Yang、Lei Shi、Chang-Fang Zhou、Hai-Liang Zhu

  DOI：10.1016/j.bmc.2009.10.054

  日期：2010.1

  Two series of novel N-benzyl-N-(X-2-hydroxybenzyl)-N'-phenylureas and thioureas (1a-18a; 1b-18b) as potential EGFR and HER-2 kinase inhibitors have been discovered. These compounds displayed good EGFR and HER-2 inhibitory activity and the SARs are also been studied. Especially compound 7b demonstrated significant EGFR and HER-2 inhibitory activity (IC50 = 0.08 mu M for EGFR and IC50 = 0.35 mu M for HER-2). Docking simulation was performed to position compound 7b into the EGFR active site to determine the probable binding conformation and antiproliferative assay results indicating that these series of urea and thioureas own high antiproliferative activity against MCF-7. Above all, thiourea 7b would be a potential anticancer agent deserves further research. (C) 2009 Elsevier Ltd. All rights reserved.