N,N'-bis(3-fluorosalicylidene)-1,2-phenylenediamine | 115077-79-7

• 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: N,N'-bis(3-fluorosalicylidene)-1,2-phenylenediamine
• 英文别名: 2-Fluoro-6-[[2-[(3-fluoro-2-hydroxyphenyl)methylideneamino]phenyl]iminomethyl]phenol
• CAS: 115077-79-7
• 化学式: C₂₀H₁₄F₂N₂O₂
• 分子量: 352.34
• InChiKey: BEBMMLNTPVNBDO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 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：
  6

反应信息

• 作为反应物：
  描述：

  N,N'-bis(3-fluorosalicylidene)-1,2-phenylenediamine 、 bis(N,N'-di(salicylidene)-2-hydroxyphenylmethanediaminato)zirconium(IV) 以 二氯甲烷 为溶剂， 生成 (N,N'-di(salicylidene)-2-hydroxyphenylmethanediaminato)(N,N'-di(3-fluorosalicylidene)-1,2-phenylenediaminato)zirconium(IV)
  参考文献：
  名称：

  具有6、4、6元螯合环的席夫碱配合物双（N，N'-双（2-羟基亚苄基）-2-羟基苯基甲烷二氨基）锆（IV）的合成，结构和反应活性

  摘要：

  通过加热摩尔比为1：2的Zr（OBu n）4已成功制备了标题配合物Zr（dshpm）2以及游离乙醇中的游离配体。它是单核的，在十二面体配位范围内为八个坐标。两个O，N，N，O供体原子四齿席夫碱配体各自形成6,4,6-元螯合环。如所预期的，如加热溶液的TLC和NMR及其随后的化学反应所示，螯合环尺寸从6,5,6-改变为6,4,6-导致复合物更加不稳定。预计不会比ZrN平均键距短0.010Å，这似乎是由于锆原子偏爱氧原子占据某些位置而产生的。由标题复合物制备两种杂合性复合物以评估标题化合物作为合成子的潜力。还制备了一种新的氟取代的均化席夫碱Zr配合物，出于比较目的。尽管Zr（dshpm）具有合理的稳定性如图2所示，在空气中，在硅胶上和在加热的溶液中，经过稀释的Hdshpm（2-）配体的分解会干扰所需杂合剂产物的纯化。

  DOI：

  10.1016/s0277-5387(01)00979-2
• 作为产物：
  描述：

  3-氟-2-羟基苯甲醛 、 邻苯二胺 以 甲醇 为溶剂， 反应 3.0h， 生成 N,N'-bis(3-fluorosalicylidene)-1,2-phenylenediamine
  参考文献：
  名称：

  含席夫碱配体的单核钌（II）配合物催化高效水氧化

  摘要：

  合成了四种新的含双价Schiff碱和异喹啉或4-甲基吡啶配体的电荷中性钌（II）配合物，并通过NMR和ESI-MS光谱，元素分析和X射线衍射对其进行了表征。使用（NH 4）2 Ce（NO 3）6作为牺牲电子受体，该配合物在酸性条件下（pH 1.0）表现出优异的化学水氧化活性和高稳定性。这些配合物在低浓度下对水氧化的高催化活性可维持超过10小时。实现了高达3200个的高周转率。提出了一种水亲核攻击机制。汝五高分辨质谱法在催化循环中检测到了O中间体。

  DOI：

  10.1002/chem.201305011

文献信息

• Synthesis, Characterization, and in vitro Antiproliferative Activity of [Salophene]platinum(II) Complexes
  作者：Maria T. Proetto、Wukun Liu、Andrey Molchanov、William S. Sheldrick、Adelheid Hagenbach、Ulrich Abram、Ronald Gust

  DOI：10.1002/cmdc.201402123

  日期：2014.6

  series of methoxy‐ and fluorine‐substituted [salophene]platinum(II) complexes (salophene=N,N′‐bis(salicylidene)‐1,2‐phenylenediamine) were synthesized and characterized by 1H NMR spectroscopy and mass spectrometry. The structure was confirmed on the example of [5‐OCH3‐salophene]platinum(II) (4‐Pt) by crystal structure analysis. The cytotoxicity of all complexes against MCF‐7 cells showed strong dependence

  合成了一系列甲氧基和氟取代的[salophene]铂（II）配合物（salophene = N，N'-双（水杨基亚烷基）-1，2-苯二胺），并通过1 H NMR光谱和质谱进行了表征。通过晶体结构分析，以[5-OCH 3 - salophene]铂（II）（4 -Pt）为例确定了结构。所有复合物对MCF-7细胞的细胞毒性都显示出对取代基的种类及其在水杨叉基部分上的位置的强烈依赖性，而1- Pt（H），3 -Pt（4-OCH 3）和6- Pt（3 ‐F）表现出很高的抗增殖作用（IC 50 <2μM）。分析了药物的亲脂性和细胞蓄积性，试图解释抗肿瘤效力的差异。为了深入了解它们的作用方式，进行了DNA相互作用研究，其中未检测到嵌入或DNA共价结合的化合物，例如1 -Pt充当非DNA结合的铂类抗癌药。
• Fluorinated Fe(III) Salophene Complexes: Optimization of Tumor Cell Specific Activity and Utilization of Fluorine Labeling for in Vitro Analysis
  作者：Irene Würtenberger、Valeria Follia、Fanni Lerch、Christiane Cwikla、Nathalie Fahrner、Christina Kalchschmidt、Brigitte Flögel、Brigitte Kircher、Ronald Gust

  DOI：10.1021/jm500986h

  日期：2015.1.22

  Fluorine-substituted iron(III) salophene complexes (salophene = N,N'-bis(salicylidene)-1,2-phenylenediamine) were synthesized and evaluated for biological activity. All complexes showed growth inhibitory effects with IC50 values ranging from 0.05 to 2.45 mu M against HT-29 colon carcinoma as well as MCF-7 and MDA-MB-231 mammary carcinoma cells (cisplatin: 5.75, 12.72, 5.81 mu M, respectively). HR-CS MAS investigations revealed that the complexes were highly protein-bound already after an incubation period of 10 min and accumulated more effectively in tumor cells than cisplatin. Interestingly, the ligands were enriched in the cells too, indicating that the salophene moiety acts as a carrier ligand and mediates the uptake of the complexes. Furthermore, induction of apoptosis proved to be dependent on the substitution pattern as well as on the tumor cell line, as evidenced from the annexin V-FITC/PI assay. Most of the complexes, especially the highly active 5-Fe, showed tumor cell specific effects and no/less influence on the proliferation of T-cells generated from the peripheral blood of healthy individuals.
• Functional Derivatives of [4‐Amino‐<i>N</i>,<i>N</i>′‐<i>bis</i>(2‐hydroxybenzidene)‐1,2‐phenylenediaminato][<i>N</i>,<i>N</i>′‐<i>bis</i>(2‐hydroxybenzidene)‐1,2‐phenylenediaminato]zirconium(IV), Zr(adsp)(Rdsp), for Use as Pendent Groups
  作者：Marvin L. Illingsworth、Wei Wang、Kenneth A. Hughes、John A. Terschak、Jonathan P. McCarney、Russell A. Stapleton、Shawn R. Wagner、Kari J. Trotter、Raymond E. Courtney、Russel A. Giacofei、Andrew J. Jensen、Marc S. Moisa、Todd A. Browning、Birgit E. Puchebner、Carla A. Theimer、Yang Chen

  DOI：10.1081/sim-120030443

  日期：2004.3

  The objective of this research was to prepare a variety of functional group derivatives of the eight-coordinate complex [4-amino-N,N'-bis(2-hydroxybenzidene)-1,2-phenytenediaminato] [N,N'-bis(2-hydroxybenzidene)-1,2-phenylenediaminato]zirconium(IV), Zr(adsp)(dsp), for use as pendent groups on polymers. The synthetic method involved reaction of the free ligands di-2-hydroxybenzylidene-4-nitro-N,N'-phenylenediamine [H-2(ndsp)] and a functional group derivative of di-2-hydroxybenzylidene-N,N'-phenylenediamine [H-2(Rdsp), R = methyl, 3-methoxy, 5-methoxy, cyano, pyridyl nitrogen, and 3-fluoro substituents] with zirconium tetra-n-butoxide in I : I : I mole ratio, followed by column separation on silica gel and hydrogenation of the nitro group to amino group using hydrogen gas over Pd/C catalyst. The order of the latter two steps was chosen to affect the best column separation. Elemental analyses, physical data, FT-IR, and NMR spectral data for six new Zr(adsp)(Rdsp) complexes are reported. Eleven new Zr(ndsp)(Rdsp) and related homoleptic complexes are also included to corroborate spectral assignments.
• Chen, Dian; Martell, Arthur E.; Sun, Yizhen, Inorganic Chemistry, 1989, vol. 28, # 13, p. 2647 - 2652
  作者：Chen, Dian、Martell, Arthur E.、Sun, Yizhen

  DOI：——

  日期：——