(4-Bromo-phenyl)-[1-(3-bromo-phenyl)-meth-(E)-ylidene]-amine | 62305-67-3

• 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: (4-Bromo-phenyl)-[1-(3-bromo-phenyl)-meth-(E)-ylidene]-amine
• 英文别名: Benzenamine, 4-bromo-N-[(3-bromophenyl)methylene]-；1-(3-bromophenyl)-N-(4-bromophenyl)methanimine
• CAS: 62305-67-3
• 化学式: C₁₃H₉Br₂N
• 分子量: 339.029
• InChiKey: NUVWQLGISUEJKS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  16
• 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：
  12.4
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (4-Bromo-phenyl)-[1-(3-bromo-phenyl)-meth-(E)-ylidene]-amine 在 sodium tetrahydroborate 、 氯化亚砜 、 盐酸羟胺 、 potassium hydroxide 作用下， 以 1,4-二氧六环 、 甲醇 为溶剂， 生成 N¹-(3-bromobenzyl)-N⁷-hydroxy-N¹-(4-bromophenyl)heptanediamide
  参考文献：
  名称：

  Design and Optimization of Novel Hydroxamate-Based Histone Deacetylase Inhibitors of Bis-Substituted Aromatic Amides Bearing Potent Activities against Tumor Growth and Metastasis

  摘要：

  Histone deacetylases (HDACs) are one of the most promising drug targets for cancer therapy, and since more than 90% of all cancer-related deaths are associated with tumor metastasis, developing strategies to inhibit tumor metastasis while retaining anti-tumor growth activity are of great interest. Herein we demonstrated the design and identification of a series of novel hydroxamate-based HDAC inhibitors bearing potent activities against tumor growth and metastasis. Optimization of the initial hit resulted in the discovery of new HDAC inhibitors through studying the structureactivity relationship. Among them, compound 11b, one of the most potent leads, exhibited nanomolar IC50 values toward inhibition of class I and IIb HDACs as well as sub-micromolar activity against proliferation and migration of breast cancer cells in vitro. More importantly, it also significantly suppressed tumor growth in a breast tumor xenograft mouse model and dose-dependently blocked in vivo tumor metastasis in a mouse pulmonary metastasis model.

  DOI：

  10.1021/jm5012148
• 作为产物：
  描述：

  间溴苯甲醛 、 4-溴苯胺 以 乙醇 为溶剂， 生成 (4-Bromo-phenyl)-[1-(3-bromo-phenyl)-meth-(E)-ylidene]-amine
  参考文献：
  名称：

  供体-受体氮丙啶和亚胺的对映选择性 [3+2] 环加成反应构建 2,5-反式咪唑啉

  摘要：

  报道了与2,2'-二酯氮丙啶和亚胺合成咪唑啉化合物的不对称[3+2]环化。在温和的反应条件下，以高产率和出色的对映选择性获得了一系列手性反式咪唑啉。与之前报道的咪唑啉类化合物的合成方法相比，该方法可以提供具有2,5-反式选择性的咪唑啉类化合物。产物的立体选择性由金属/ N、N'-二氧化物和对照实验表明的底物相互作用决定。

  DOI：

  10.1002/chem.202203757

文献信息

• Synthesis of potential medicinal compounds based on hydrophosphoryl compounds. II. Arylammonium N-substituted-1-aminoarylmethanephosphinate salts
  作者：V. I. Yudelevich、L. B. Sokolov、B. I. Ionin、E. V. Komarov、G. A. Mikhailets、L. G. Myasnikova、G. E. Grinberg

  DOI：10.1007/bf00773090

  日期：1982.8
• Design and Optimization of Novel Hydroxamate-Based Histone Deacetylase Inhibitors of Bis-Substituted Aromatic Amides Bearing Potent Activities against Tumor Growth and Metastasis
  作者：Feifei Yang、Tao Zhang、Haigang Wu、Yang Yang、Ning Liu、Ang Chen、Qiang Li、Jingjie Li、Liwen Qin、Beier Jiang、Xin Wang、Xiufeng Pang、Zhengfang Yi、Mingyao Liu、Yihua Chen

  DOI：10.1021/jm5012148

  日期：2014.11.26

  Histone deacetylases (HDACs) are one of the most promising drug targets for cancer therapy, and since more than 90% of all cancer-related deaths are associated with tumor metastasis, developing strategies to inhibit tumor metastasis while retaining anti-tumor growth activity are of great interest. Herein we demonstrated the design and identification of a series of novel hydroxamate-based HDAC inhibitors bearing potent activities against tumor growth and metastasis. Optimization of the initial hit resulted in the discovery of new HDAC inhibitors through studying the structureactivity relationship. Among them, compound 11b, one of the most potent leads, exhibited nanomolar IC50 values toward inhibition of class I and IIb HDACs as well as sub-micromolar activity against proliferation and migration of breast cancer cells in vitro. More importantly, it also significantly suppressed tumor growth in a breast tumor xenograft mouse model and dose-dependently blocked in vivo tumor metastasis in a mouse pulmonary metastasis model.
• Enantioselective [3+2] Cycloaddition of Donor‐Acceptor Aziridines and Imines to Construct 2,5‐ <i>trans</i> ‐Imidazolidines
  作者：Jianglin Qiao、Shiyu Wang、Xiaohua Liu、Xiaoming Feng

  DOI：10.1002/chem.202203757

  日期：2023.3.28

  An asymmetric [3+2] annulation to synthesize imidazolidine compounds with 2,2’-diester aziridines and imines was reported. A series of chiral trans-imidazolidines were obtained in high yields with outstanding enantioselectivities under mild reaction conditions. Compared to the previously reported method of synthesizing imidazolines, this method could offer the imidazoline compounds with 2,5-trans-selectivity

  报道了与2,2'-二酯氮丙啶和亚胺合成咪唑啉化合物的不对称[3+2]环化。在温和的反应条件下，以高产率和出色的对映选择性获得了一系列手性反式咪唑啉。与之前报道的咪唑啉类化合物的合成方法相比，该方法可以提供具有2,5-反式选择性的咪唑啉类化合物。产物的立体选择性由金属/ N、N'-二氧化物和对照实验表明的底物相互作用决定。