3,3"-dinitro-2',3'-dimethoxy-4,4"-dihydroxy[1,1':4',1"-terphenyl]

• 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: 3,3"-dinitro-2',3'-dimethoxy-4,4"-dihydroxy[1,1':4',1"-terphenyl]
• 英文别名: 4-[4-(4-Hydroxy-3-nitrophenyl)-2,3-dimethoxyphenyl]-2-nitrophenol；4-[4-(4-hydroxy-3-nitrophenyl)-2,3-dimethoxyphenyl]-2-nitrophenol
• 化学式: C₂₀H₁₆N₂O₈
• 分子量: 412.356
• InChiKey: UCRUDILFMPEHCJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  30
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  151
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  4-溴-2-硝基苯酚 在 potassium fluoride dihydrate 、 potassium acetate 作用下， 以 1,4-二氧六环 为溶剂， 反应 0.34h， 生成 4,4'-二羟基-3,3'-二硝基联苯 、 3,3"-dinitro-2',3'-dimethoxy-4,4"-dihydroxy[1,1':4',1"-terphenyl]
  参考文献：
  名称：

  Synthesis, biological evaluation and modeling studies of terphenyl topoisomerase IIα inhibitors as anticancer agents

  摘要：

  We report the synthesis and evaluation of a series of novel terphenyls. Compound 17 had the most potent anticancer activity, indicating that the phenolic hydroxyl was a key group. A DNA relaxation test showed that compound 17 had a strong inhibitory effect on TOP2 alpha, but not on TOP1, which was consistent with the docking analysis results. We performed a 3D-QSAR study using CoMFA and CoMSIA to determine, for the first time, the chemical-biological relationship in the inhibition of TOP by terphenyls. The CoMFA and CoMSIA model had good modeling statistics: leave-one-out q(2) of 0.605 and 0.622, r(2) of 0.998 and 0.994, and r(2), pred (test set) of 0.742 and 0.660. These results suggest that the ortho-phenolic hydroxyl on ring A is important for producing terphenyls with more efficacious activity. (C) 2015 Elsevier Masson SAS. All rights. reserved.

  DOI：

  10.1016/j.ejmech.2015.03.010