N,N'-bis(2-hydroxynaphthylidene)-4-carboxy-1,2-phenylenediamine

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: N,N'-bis(2-hydroxynaphthylidene)-4-carboxy-1,2-phenylenediamine
• 英文别名: 3,4-Bis[(2-hydroxynaphthalen-1-yl)methylideneamino]benzoic acid；3,4-bis[(2-hydroxynaphthalen-1-yl)methylideneamino]benzoic acid
• 化学式: C₂₉H₂₀N₂O₄
• 分子量: 460.489
• InChiKey: AHBASTQKCCKDMQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  35
• 可旋转键数：
  5
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  103
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  potassium tetrachloroplatinate(II) 、 N,N'-bis(2-hydroxynaphthylidene)-4-carboxy-1,2-phenylenediamine 在 potassium acetate 作用下， 以 二甲基亚砜 、 N,N-二甲基甲酰胺 为溶剂， 反应 12.0h， 以68%的产率得到
  参考文献：
  名称：

  New platinum and ruthenium Schiff base complexes for water splitting reactions

  摘要：

  新的 Pt(II) 和 Ru(II) 配合物与席夫碱配体展示出有效的可见光催化水还原和 Ce4+ 驱动的氧化活性。

  DOI：

  10.1039/c5dt01055a
• 作为产物：
  描述：

  2-羟基-1-萘甲醛 、 3,4-二氨基苯甲酸 在 氯化锌四氢呋喃配合物（1：2） 作用下， 以 四氢呋喃 为溶剂， 反应 5.0h， 以91%的产率得到N,N'-bis(2-hydroxynaphthylidene)-4-carboxy-1,2-phenylenediamine
  参考文献：
  名称：

  New platinum and ruthenium Schiff base complexes for water splitting reactions

  摘要：

  新的 Pt(II) 和 Ru(II) 配合物与席夫碱配体展示出有效的可见光催化水还原和 Ce4+ 驱动的氧化活性。

  DOI：

  10.1039/c5dt01055a

文献信息

• Synthesis, characterization, anticancer activity, thermal and electrochemical studies of some novel uranyl Schiff base complexes
  作者：Zahra Asadi、Mozaffar Asadi、Fahimeh Dehghani Firuzabadi、Reza Yousefi、Mehrnaz Jamshidi

  DOI：10.1007/s13738-013-0314-5

  日期：2014.4

  Some tetradentate N2O2 Schiff base ligands, such as N,N′-bis(naphtalidene)-1,2-phenylenediamine, N,N′-bis(naphtalidene)-4-methyl-1,2-phenylenediamine, N,N′-bis(naphtalidene)-4-chloro-1,2-phenylenediamine, N,N′-bis(naphtalidene)-4-nitro-1,2-phenylenediamine, N,N′-bis(naphtalidene)-4-carboxyl-1,2-phenylenediamine, and their uranyl complexes were synthesized and characterized by 1H NMR, IR, UV–Vis spectroscopy, TG (thermogravimetry), and elemental analysis (C.H.N.). Thermogravimetric analysis shows that uranyl complexes have very different thermal stabilities. This method is used also to establish that only one solvent molecule is coordinated to the central uranium ion and this solvent molecule does not coordinate strongly and is removed easier than the tetradentate ligand and also trans oxides. The electrochemical properties of the uranyl complexes were investigated by cyclic voltammetry. Electrochemistry of these complexes showed a quasireversible redox reaction without any successive reactions. Also, the kinetic parameters of thermal decomposition were calculated using Coats–Redfern equation. According to Coats–Redfern plots the kinetics of thermal decomposition of the studied complexes is first-order in all stages. Anticancer activity of the uranyl Schiff base complexes against cancer cell lines (Jurkat) was studied and determined by MTT (3-[4,5-dimethylthiazol-2-yl]-2,5-diphenyltetrazoliumbromide) assay.

  一些四价 N2O2 席夫碱配体，如 N,N′-双(萘)-1,2-苯二胺、N,N′-双(萘)-4-甲基-1、N,N′-双(萘)-4-甲基-1,2-苯二胺、N,N′-双(萘)-4-氯-1,2-苯二胺、N,N′-双(萘)-4-硝基-1、合成了 N,N′-双(萘)-4-羧基-1,2-苯二胺、N,N′-双(萘)-4-硝基-1,2-苯二胺、N,N′-双(萘)-4-硝基-1,2-苯二胺、N,N′-双(萘)-4-羧基-1,2-苯二胺及其铀酰配合物，并通过 1H NMR、IR、UV-Vis 光谱、TG（热重）和元素分析（C.H.N.）。热重分析表明，铀酰配合物的热稳定性大不相同。利用这种方法还可以确定，只有一个溶剂分子与中心铀离子配位，而且该溶剂分子的配位不强，比四价配体和反式氧化物更容易去除。通过循环伏安法研究了铀酰配合物的电化学特性。这些络合物的电化学反应显示出一种准可逆的氧化还原反应，没有任何连续反应。此外，还利用 Coats-Redfern 方程计算了热分解的动力学参数。根据 Coats-Redfern 图，所研究复合物的热分解动力学在所有阶段都是一阶的。通过 MTT（3-[4,5-二甲基噻唑-2-基]-2,5-二苯基四唑溴化物）测定法研究并确定了铀酰希夫碱复合物对癌细胞株（Jurkat）的抗癌活性。
• Evaluation of photochemotherapeutic potential of a few oxo-bridged dimeric Fe(III) compounds having Salen-type ligands
  作者：Dhananjay Das、Md Kausar Raza、Tridib K. Goswami

  DOI：10.1016/j.poly.2020.114614

  日期：2020.8

  Four oxo-bridged dimeric Fe(III) complexes, viz. [(mu-O)Fe(L)}(2)] (1-4), where L is N,N '-bis(naphtalidene)ethylenediamine, (H2L1 in 1); N,N '-bis(naphtalidene)-1,2-phenylenediamine, (H2L2 in 2); N,N '-bis(naphtalidene)-4-nitro-1,2-phenylenediamine (H2L3 in 3) and N,N '-bis(naphtalidene)-4-carboxyl-1,2-phenylenediamine, (H2L4 in 4) were synthesized for their potential application as photochemotherapeutic agents in low energy visible light. The solid-state structure of complex 2 was confirmed by X-ray crystallography. The complexes bind to human serum albumin (HSA) reversibly in a pH dependent manner, which could be a potential carrier of the molecules in blood plasma. They also bind to calf-thymus (ct) DNA with considerable affinity. In vitro cellular experiments show that the complexes display significant photo-enhanced cytotoxicity in human cervical cancer (HeLa) and human breast cancer (MCF-7 and MDA-MB-231) cells with low dark toxicity. ICP-MS analysis show that the complexes enter HeLa cells in a dose-dependent manner. Flow cytometric and confocal microscopic experiments demonstrate that the complexes kill cancer cells on exposure to visible light primarily via apoptosis through the generation of reactive oxygen species (ROS). (C) 2020 Elsevier Ltd. All rights reserved.