meso-3,4-bis(4-fluorophenyl)-1,6-bis(2-hydroxy-6-methoxyphenyl)-2,5-diazahexa-1,5-diene | 1382482-46-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: meso-3,4-bis(4-fluorophenyl)-1,6-bis(2-hydroxy-6-methoxyphenyl)-2,5-diazahexa-1,5-diene
• CAS: 1382482-46-3
• 化学式: C₃₀H₂₆F₂N₂O₄
• 分子量: 516.544
• InChiKey: JPXUTDQDYNXPGM-RNPORBBMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.41
• 重原子数：
  38.0
• 可旋转键数：
  9.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  83.64
• 氢给体数：
  2.0
• 氢受体数：
  6.0

反应信息

• 作为产物：
  描述：

  2-羟基-6-甲氧基苯甲醛 、 meso-1,2-bis(4-fluorophenyl)-1,2-ethanediamine 以 乙腈 为溶剂， 反应 6.0h， 以83%的产率得到meso-3,4-bis(4-fluorophenyl)-1,6-bis(2-hydroxy-6-methoxyphenyl)-2,5-diazahexa-1,5-diene
  参考文献：
  名称：

  Synthesis, characterization and in vitro antitumour activity of a series of novel platinum(II) complexes bearing Schiff base ligands

  摘要：

  A series was neutral platinum(II) complexes bearing OCH3- or F-substituted 3,4-bis(4-fluorophenyl)-1,6-bis(2-hydroxyphenyl)-2,5-diazahexa-1,5-dienes (diarylsalenes) were synthesized and tested for in vitro antitumour activity. The growth inhibitory effects depended on the configuration and the substitution pattern of the salicylidene moiety. The lead compound [meso-3,4-bis(4-fluorophenyl)-1,6-bis(2-hydroxyphenyl)-2,5-diazahexa-1,5-diene]platinum(II) (1-Pt) reduced the cell growth of MCF-7 (IC50 = 7.6 mu M) and MDA-MB 231 cells (IC50 = 10.0 mu M), but was inactive against HT-29 cells at the used concentration range (IC50 > 20 mu M). The change of the configuration (meso -> d,l) at the 1,2-diimino-1,2-diarylethane bridge and methoxy substitution led to completely inactive compounds, while fluorine substituents increased the antiproliferative effects depending on their position (3-F < 5-F < 4-F < 6-F). Complex 10-Pt (6-F: IC50(MCF-7) = 1.5 mu M, IC50(MDA-MB 231) = 1.3 mu M, IC50 (HT-29) = 2.6 mu M) was as active as cisplatin (IC50(MCF-7) = 1.6 mu M, IC50(MDA-MB 231) = 1.5 mu M, IC50(HT-29) = 4.1 mu M). (C) 2012 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2012.03.053