2-Bromo-6-[[2-[(3-bromo-2-hydroxyphenyl)methylideneamino]phenyl]iminomethyl]phenol | 1354637-49-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 2-Bromo-6-[[2-[(3-bromo-2-hydroxyphenyl)methylideneamino]phenyl]iminomethyl]phenol
• CAS: 1354637-49-2
• 化学式: C₂₀H₁₄Br₂N₂O₂
• 分子量: 474.151
• InChiKey: KLNWYNZQKDUAOK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  26
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  65.2
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  Ti(2,6-dimethylphenoxide)4 、 2-Bromo-6-[[2-[(3-bromo-2-hydroxyphenyl)methylideneamino]phenyl]iminomethyl]phenol 以 四氢呋喃 为溶剂， 以81%的产率得到
  参考文献：
  名称：

  Cytotoxicity and Hydrolysis of trans-Ti(IV) Complexes of Salen Ligands: Structure–Activity Relationship Studies

  摘要：

  Eleven bis(dimethylphenolato) Ti(IV) complexes of salen ligands with different steric and electronic properties due to different aromatic substituents at the ortho and para positions are reported, and their cytotoxicity toward HT-29 and OVCAR-1 cells and its dependence on hydrolytic behavior are discussed. Eight complexes of this series were analyzed by X-ray crystallography, confirming the trans geometry of the labile ligands with otherwise relatively similar coordination features to those of cis-salan analogues. Relatively high and similar hydrolytic stability is observed for all complexes, with t(1/2) values for labile ligand hydrolysis of 2-11 h in 10% D2O solutions. In contrast, varying cytotoxicities were achieved, identifying selected members as the first trans-Ti(IV) complexes reported as anticancer agents. Steric bulk all around the complex diminished the activity, where a complex with no aromatic substitutions is especially active and complexes substituted particularly at the ortho positions are mostly inactive, including ortho-halogenated and ortho-tert-butylated, with one exception of the ortho-methoxylated complex demonstrating appreciable activity. In contrast, para-halogenation provided the complexes of highest cytotoxic activity in this series (IC50 as low as 1.0 +/- 0.3 mu M), with activity exceeding that of cisplatin by up to 15-fold. Reaction of a representative complex with ortho-catechol yielded a "cis"Ti(IV) complex following rearrangement of the salen ligand on the metal center, with highly similar coordination features and geometry to those of the catecholato salan analogues, suggesting that the complexes operate by similar mechanisms and rearrangement of the salen ligand may occur upon introduction of a suitable chelating target. In additional cytotoxicity measurements, a salen complex was preincubated in the biological medium for varying periods prior to cell addition, revealing that marked cytotoxicity of the salen complex is retained for longer preincubation periods relative to known Ti(IV) complexes, suggesting that the hydrolysis products may also induce cytotoxic effects, thus reducing stability concerns.

  DOI：

  10.1021/ic202092u