N-(5-bromo-2-thienylmethyl)-2-methoxyaniline

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: N-(5-bromo-2-thienylmethyl)-2-methoxyaniline
• 英文别名: N-[(5-bromothiophen-2-yl)methyl]-2-methoxyaniline
• 化学式: C₁₂H₁₂BrNOS
• mdl: MFCD11141333
• 分子量: 298.203
• InChiKey: MWUXMMOWDPLZDA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.166
• 拓扑面积：
  49.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-(5-bromo-2-thienylmethyl)-2-methoxyaniline 在 氯化亚砜 作用下， 以 1,4-二氧六环 为溶剂， 反应 10.0h， 生成 N-((5-bromo-2-thiopheneyl)methyl)-N-(2-methoxyphenyl)pimelic acid methyl ester
  参考文献：
  名称：

  杂环取代异羟肟酸类芳香酰胺化合物或其药 学上可接受的盐、及其制备方法和应用

  摘要：

  本发明公开了一种式(I)所示的杂环取代异羟肟酸类芳香酰胺化合物及其药学上可接受的盐，以及其作为新型的羟肟酸类组蛋白去乙酰化酶抑制剂的应用。本发明还公开了含有本发明式(I)化合物或其药物组合物在制备预防和／或治疗由于组蛋白乙酰化失调引起的疾病的药物中的用途、以及其在制备治疗各种恶性肿瘤生长、转移和复发等疾病的药物中的应用。

  公开号：

  CN103951649B
• 作为产物：
  描述：

  邻甲氧基苯胺 在 sodium tetrahydroborate 作用下， 以 乙醇 为溶剂， 生成 N-(5-bromo-2-thienylmethyl)-2-methoxyaniline
  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