2,4-Dibromo-6-[[2-[(2-hydroxy-5-nitrophenyl)methyl-methylamino]ethyl-methylamino]methyl]phenol | 1337957-42-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 2,4-Dibromo-6-[[2-[(2-hydroxy-5-nitrophenyl)methyl-methylamino]ethyl-methylamino]methyl]phenol
• CAS: 1337957-42-2
• 化学式: C₁₈H₂₁Br₂N₃O₄
• 分子量: 503.19
• InChiKey: GFENESHPMFADIP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  27
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  92.8
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  titanium(IV) isopropylate 、 2,4-Dibromo-6-[[2-[(2-hydroxy-5-nitrophenyl)methyl-methylamino]ethyl-methylamino]methyl]phenol 以 四氢呋喃 为溶剂， 生成 2,4-Dibromo-6-[[methyl-[2-[methyl-[(5-nitro-2-oxidophenyl)methyl]amino]ethyl]amino]methyl]phenolate;propan-2-olate;titanium(4+)
  参考文献：
  名称：

  具有不同取代芳环的Salan配体的C 1-对称的钛（IV）配合物：增强的细胞毒活性

  摘要：

  合成了不同取代的芳环的二氨基双（酚基）（“ salan”）钛（IV）配合物，并对其水解稳定性和细胞毒性进行了分析，并与C 2-对称类似物及其等摩尔混合物进行了比较。不对称复合物的水解稳定性介于对称类似物的水解稳定性之间，这暗示了配体结构参数的累加影响。相对于对称类似物及其混合物，大多数混合的卤化/硝化复合物显示出明显的细胞毒性，IC 50为值低至<1μM，相当于活性超过顺铂高达30倍。相反，具有相似性质的取代的不对称复合物揭示了两者的附加影响，并且在对称类似物之间具有细胞毒性。在假定活性物质通常是多核水解产物的前提下，总体看来，特定的配体设计和包括亲水性和疏水性在内的影响参数的微调对于最大限度地提高生物效率至关重要。

  DOI：

  10.1021/ic500001j
• 作为产物：
  描述：

  2-氯甲基-4-硝基苯酚 、 2,4-dibromo-6-((methyl(2-(methylamino)ethyl)amino)methyl)phenol 在 三乙胺 作用下， 以 四氢呋喃 为溶剂， 以42%的产率得到2,4-Dibromo-6-[[2-[(2-hydroxy-5-nitrophenyl)methyl-methylamino]ethyl-methylamino]methyl]phenol
  参考文献：
  名称：

  A Marked Synergistic Effect in Antitumor Activity of Salan Titanium(IV) Complexes Bearing Two Differently Substituted Aromatic Rings

  摘要：

  Salan titanium(IV) complexes of differently substituted aromatic rings, where one ring is para-nitrated and another is ortho,para-halogenated, demonstrate exceptionally high anticancer activity, with IC50 values of <1 mu M, exceeding that of cisplatin by similar to 30-fold. Whereas an additive effect in hydrolytic stability was detected for these highly stable complexes, an unexpected synergistic effect in anticancer activity makes these hybrid complexes substantially more active than both their symmetrical analogues alone and their equimolar mixture.

  DOI：

  10.1021/ja208219f

文献信息

• <i>C</i>₁-Symmetrical Titanium(IV) Complexes of Salan Ligands with Differently Substituted Aromatic Rings: Enhanced Cytotoxic Activity
  作者：Hagai Glasner、Edit Y. Tshuva

  DOI：10.1021/ic500001j

  日期：2014.3.17

  Diaminobis(phenolato) (“salan”) titanium(IV) complexes of differently substituted aromatic rings were synthesized, and their hydrolytic stability and cytotoxicity were analyzed and compared to those of the C2-symmertrical analogues and their equimolar mixtures. The hydrolytic stability of the asymmetrical complexes was in between those of the symmetrical analogues, implying an additive influence of the ligand structural

  合成了不同取代的芳环的二氨基双（酚基）（“ salan”）钛（IV）配合物，并对其水解稳定性和细胞毒性进行了分析，并与C 2-对称类似物及其等摩尔混合物进行了比较。不对称复合物的水解稳定性介于对称类似物的水解稳定性之间，这暗示了配体结构参数的累加影响。相对于对称类似物及其混合物，大多数混合的卤化/硝化复合物显示出明显的细胞毒性，IC 50为值低至<1μM，相当于活性超过顺铂高达30倍。相反，具有相似性质的取代的不对称复合物揭示了两者的附加影响，并且在对称类似物之间具有细胞毒性。在假定活性物质通常是多核水解产物的前提下，总体看来，特定的配体设计和包括亲水性和疏水性在内的影响参数的微调对于最大限度地提高生物效率至关重要。
• A Marked Synergistic Effect in Antitumor Activity of Salan Titanium(IV) Complexes Bearing Two Differently Substituted Aromatic Rings
  作者：Hagai Glasner、Edit Y. Tshuva

  DOI：10.1021/ja208219f

  日期：2011.10.26

  Salan titanium(IV) complexes of differently substituted aromatic rings, where one ring is para-nitrated and another is ortho,para-halogenated, demonstrate exceptionally high anticancer activity, with IC50 values of <1 mu M, exceeding that of cisplatin by similar to 30-fold. Whereas an additive effect in hydrolytic stability was detected for these highly stable complexes, an unexpected synergistic effect in anticancer activity makes these hybrid complexes substantially more active than both their symmetrical analogues alone and their equimolar mixture.