5-Fluoro-2-[2-(5-fluoro-3-oxo-1,2-benzoselenazol-2-yl)ethyl]-1,2-benzoselenazol-3-one | 1381781-87-8

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 芳基卤化物
• 英文名称: 5-Fluoro-2-[2-(5-fluoro-3-oxo-1,2-benzoselenazol-2-yl)ethyl]-1,2-benzoselenazol-3-one
• CAS: 1381781-87-8
• 化学式: C₁₆H₁₀F₂N₂O₂Se₂
• 分子量: 458.184
• InChiKey: FRYLJQGCOCBGLG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.41
• 重原子数：
  24
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  40.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  2-氨基-5-氟苯甲酸 在 盐酸 、 氯化亚砜 、 三乙胺 、 sodium nitrite 作用下， 以 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 6.0h， 生成 5-Fluoro-2-[2-(5-fluoro-3-oxo-1,2-benzoselenazol-2-yl)ethyl]-1,2-benzoselenazol-3-one
  参考文献：
  名称：

  Inhibition of thioredoxin reductase by a novel series of bis-1,2-benzisoselenazol-3(2H)-ones: Organoselenium compounds for cancer therapy

  摘要：

  Thioredoxin reductase (TrxR) is critical for cellular redox regulation and is involved in tumor proliferation, apoptosis and metastasis. Its C-terminal redox-active center contains a cysteine (Cys497) and a unique selenocysteine (Sec498), which are exposed to solvent and easily accessible. Thus, it is becoming an important target for anticancer drugs. Selective inhibition of TrxR by 1,2-(bis-1,2-benzisoselenazol-3(2H)-one)ethane (4a) prevents proliferation of several cancer cell lines both in vivo and in vitro. Using the structure of 4a as a starting point, a series of novel bis-1,2-benzisoselenazol-3(2H)-ones was designed, prepared and tested to explore the structure-activity relationships (SARs) for this class of inhibitor and to improve their potency. Notably, 1,2-(5,5'-dimethoxybis(1,2-benzisoselenazol-3(2H)-one))ethane (12) was found to be more potent than 4a in both in vitro and in vivo evaluation. Its binding sites were confirmed by biotin-conjugated iodoacetamide assay and a SAR model was generated to guide further structural modification. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2012.04.033