2-hydroxy-3-(((2-hydroxybenzyl)(pyridin-2-ylmethyl)amino)methyl)-5-methylbenzaldehyde

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-hydroxy-3-(((2-hydroxybenzyl)(pyridin-2-ylmethyl)amino)methyl)-5-methylbenzaldehyde
• 英文别名: 3-[N,N-(2-pyridylmethyl)(2-hydroxybenzyl)aminomethyl]-5-methylsalicylaldehyde；2-Hydroxy-3-[[(2-hydroxyphenyl)methyl-(pyridin-2-ylmethyl)amino]methyl]-5-methylbenzaldehyde；2-hydroxy-3-[[(2-hydroxyphenyl)methyl-(pyridin-2-ylmethyl)amino]methyl]-5-methylbenzaldehyde
• 化学式: C₂₂H₂₂N₂O₃
• 分子量: 362.428
• InChiKey: YCXJIELMORQJFS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  27
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  73.7
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-hydroxy-3-(((2-hydroxybenzyl)(pyridin-2-ylmethyl)amino)methyl)-5-methylbenzaldehyde 、 5-苯基异噻唑-3-羧酸酰肼 以 甲醇 、 二氯甲烷 为溶剂， 反应 3.0h， 以96%的产率得到
  参考文献：
  名称：

  异恶唑衍生的芳酰肼及其双核铜（II）配合物对乳腺癌细胞具有抗增殖活性，并具有潜在的替代作用机制。

  摘要：

  细胞毒性对比：合成了两个芳酰肼基配体及其乙酸盐/高氯酸盐双铜配合物，并通过各种光谱和分析技术（包括X射线衍射）进行了表征。它们被证明与DNA相互作用并在乳腺癌细胞上显示出相反的细胞毒性。它们的生物学特性与它们与生物学相关的金属离子发生螯合/金属转移的能力有关。

  DOI：

  10.1002/cbic.202000122
• 作为产物：
  描述：

  3-(氯甲基)-2-羟基-5-甲基苯甲醛 、 N-(2-pyridylmethyl)-2-hydroxybenzylamine 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 生成 2-hydroxy-3-(((2-hydroxybenzyl)(pyridin-2-ylmethyl)amino)methyl)-5-methylbenzaldehyde
  参考文献：
  名称：

  含苯酚/吡啶的三足配体对铜 (II) 离子的意外配位模式：固态、溶液和 DFT 研究

  摘要：

  三足配体 HBPAMFF，即 3-[N,N-(2-pyridylmethyl)(2-hydroxybenzyl)aminomethyl]-5-methylsalicylaldehyde 与化学计量的 CuCl 2 ·2H 2 O 之间的反应提供了绿松石单核络合物 ( 1 ), 单斜晶系, 空间群 P 2 1 / c . 五配位铜位点采用稍微扭曲的方形金字塔几何形状，顶端位置被酚氧占据。对 1 的中红外吸收的综合实验-理论分析证实，HBPAMFF 中存在的两个酚基在络合后仍保持完全质子化。仍然处于固态，X 波段 EPR 光谱显示 3 g- 没有超精细展开的菱形光谱值。在乙腈 (MeCN) 和二甲基亚砜 (DMSO) 中进行了溶液研究，其中氯离子主要与铜配位，其中氯离子被铜配位层中的溶剂分子取代。电子光谱和冷冻溶液 EPR 也证实了存在于 MeCN 和 DMSO 中的物种的不同性质。这项工作揭示了有关含酚配体的金属化合物（例如

  DOI：

  10.1016/j.molstruc.2023.135827

文献信息

• Different coordination patterns for two related unsymmetrical compartmental ligands: crystal structures and IR analysis of [Cu(C₂₁H₂₁O₂N₃)(OH₂)(ClO₄)]ClO₄·2H₂O and [Zn₂(C₂₂H₂₁O₃N₂)(C₂₂H₂₀O₃N₂)]ClO₄
  作者：Aline Cruz De Moraes Reis、Maria Clara Ramalho Freitas、Jackson A.L.C. Resende、Renata Diniz、Nicolás A. Rey

  DOI：10.1080/00958972.2014.958080

  日期：2014.9.17

  complexes [Cu(HL1)(OH2)(ClO4)]ClO4·2H2O (1) and [Zn2(HL2)(L2)]ClO4 (2), derived from two related, phenol-based compartmental ligands, are described. Compound 2 constitutes the first report of a complex obtained from H2L2. The metal compounds are structurally different; 2 is a dimer in which all the heteroatoms of the ligand take part in coordination, while 1 is mononuclear containing a pair of cis-oriented

  新配合物 [Cu(HL1)(OH2)(ClO4)]ClO4·2H2O (1) 和 [Zn2(HL2)(L2)]ClO4 (2) 的晶体结构，源自两个相关的苯酚基隔室配体, 进行了说明。化合物 2 构成了从 H2L2 获得的复合物的第一份报告。金属化合物在结构上不同；2 是一个二聚体，其中配体的所有杂原子都参与配位，而 1 是单核，包含一对顺式配体，完成“开放”配位球，其中不涉及 HL1 的醛基。HL1 和 H2L2 的中心酚基的质子化状态在配合物之间也不同。对两种配合物及其各自的配体进行红外振动分析，以将观察到的光谱特征与固体的结构特性联系起来。虽然一些独特的带在络合时发生了变化，但无法通过这种技术确认芳香醛基参与配位。涉及 2 的 1H NMR 实验表明，在 d6-DMSO 中溶解后，其特定的质子化状态得以保持。图形概要
• Novel luminescent benzopyranothiophene- and BODIPY-derived aroylhydrazonic ligands and their dicopper(II) complexes: syntheses, antiproliferative activity and cellular uptake studies
  作者：Jesica Paola Rada、Jérémy Forté、Geoffrey Gontard、Claude-Marie Bachelet、Nicolás A. Rey、Michèle Salmain、Vincent Corcé

  DOI：10.1007/s00775-021-01885-5

  日期：2021.9

  the compounds showed moderate to high cytotoxicity towards the triple negative human breast cancer cell line MDA-MB-231. BPT derivatives were the most cytotoxic, specially H3L1, reaching an IC50 value up to the nanomolar range. Finally, fluorescence microscopy imaging studies employing mitochondria- and nucleus-staining dyes showed that the BODIPY-carrying ligand H3L2 was highly cell permeant and suggested

  合成并充分表征了两种新型不对称双核芳酰基腙配体和四种携带荧光苯并吡喃噻吩 (BPT) 或硼二吡咯亚甲基 (BODIPY) 实体的二铜 (II) 配合物。复合物1源自含 BPT 的配体H 3 L1，通过 X 射线衍射测量阐明了其晶体结构。讨论了所有获得的化合物的吸收和荧光曲线。此外，配体和配合物的稳定性在 DMSO 和生物相关介质中通过紫外-可见光谱监测。所有化合物对三阴性人乳腺癌细胞系 MDA-MB-231 均表现出中等至高度的细胞毒性。BPT 衍生物是最具细胞毒性的，特别是H 3 L1，达到纳摩尔范围内的IC 50值。最后，使用线粒体和细胞核染色染料的荧光显微镜成像研究表明，携带 BODIPY 的配体H 3 L2具有高度的细胞渗透性，并表明该化合物优先在线粒体中积累。 图形摘要
• Dinuclear Zinc(II) Complexes with Hydrogen Bond Donors as Structural and Functional Phosphatase Models
  作者：Simone Bosch、Peter Comba、Lawrence R. Gahan、Gerhard Schenk

  DOI：10.1021/ic5009945

  日期：2014.9.2

  It is becoming increasingly apparent that the secondary coordination sphere can have a crucial role in determining the functional properties of biomimetic metal complexes. We have therefore designed and prepared a variety of ligands as metallo-hydrolase mimics, where hydrogen bonding in the second coordination sphere is able to influence the structure of the primary coordination sphere and the substrate binding. The assessment of a structure-function relationship is based on derivates of 2,6-bis[bis(pyridin-2-ylmethyl)amino]methyl}-4-methylphenol (HBPMP = HL1) and 2-[bis(pyridin-2-ylmethyl)amino]methy1}-64[(2-hydroxybenzyl)(pyridin-2-ylmethy)amino]methyl}-4-methylphenol (H2BPBPMP = H2L5), well-known phenolate-based ligands for metallo-hydrolase mimics. The model systems provide similar primary coordination spheres but site-specific modifications in the secondary coordination sphere. Pivaloylamide and amine moieties were chosen to mimic the secondary coordination sphere of the phosphatase models, and the four new ligands H3L2, H3L3, HL4, and H4L6 vary in the type and geometric position of the H-bond donors and acceptors, responsible for the positioning of the substrate and release of the product molecules. Five dinuclear Zn-II complexes were prepared and structurally characterized in the solid, and four also in solution. The investigation phosphatase activity of four model complexes illustrates the impact of the H-bonding network: the Michaelis-Menten constants (catalyst-substrate binding) for all complexes that support hydrogen bonding are smaller than for the reference complex, and this generally leads to higher catalytic efficiency and higher turnover numbers.
• Isoxazole‐Derived Aroylhydrazones and Their Dinuclear Copper(II) Complexes Show Antiproliferative Activity on Breast Cancer Cells with a Potentially Alternative Mechanism Of Action
  作者：Jesica Paola Rada、Jéremy Forté、Geoffrey Gontard、Vincent Corcé、Michèle Salmain、Nicolás A. Rey

  DOI：10.1002/cbic.202000122

  日期：2020.9

  Cytotoxicity contrast: Two aroylhydrazonic ligands and their acetate/perchlorate dicopper complexes were synthesized and characterized by various spectroscopic and analytical techniques, including X‐ray diffraction. They were shown to interact with DNA and display contrasted cytotoxicity on breast cancer cells. Their biological properties were linked to their ability to undergo chelation/transmetallation

  细胞毒性对比：合成了两个芳酰肼基配体及其乙酸盐/高氯酸盐双铜配合物，并通过各种光谱和分析技术（包括X射线衍射）进行了表征。它们被证明与DNA相互作用并在乳腺癌细胞上显示出相反的细胞毒性。它们的生物学特性与它们与生物学相关的金属离子发生螯合/金属转移的能力有关。
• Unexpected coordination mode for a phenol/pyridine-containing tripodal ligand towards copper(II) ions: Solid state, solution and DFT Studies
  作者：Mirtes M. Damaceno、Carolina B.P. Ligiero、Jilder D.P. Serna、Odivaldo C. Alves、Luiz Antônio S. Costa、Daphne S. Cukierman、Nicolás A. Rey

  DOI：10.1016/j.molstruc.2023.135827

  日期：2023.9

  g-values rhombic spectrum without a hyperfine unfolding. Solution studies were performed in acetonitrile (MeCN), in which the chloride ions remain mostly coordinated to copper, and dimethylsulfoxide (DMSO), with the replacement of a chloride ion by a solvent molecule in the coordination sphere of copper. Electronic spectroscopy and frozen solution EPR also confirm the different nature of the species present

  三足配体 HBPAMFF，即 3-[N,N-(2-pyridylmethyl)(2-hydroxybenzyl)aminomethyl]-5-methylsalicylaldehyde 与化学计量的 CuCl 2 ·2H 2 O 之间的反应提供了绿松石单核络合物 ( 1 ), 单斜晶系, 空间群 P 2 1 / c . 五配位铜位点采用稍微扭曲的方形金字塔几何形状，顶端位置被酚氧占据。对 1 的中红外吸收的综合实验-理论分析证实，HBPAMFF 中存在的两个酚基在络合后仍保持完全质子化。仍然处于固态，X 波段 EPR 光谱显示 3 g- 没有超精细展开的菱形光谱值。在乙腈 (MeCN) 和二甲基亚砜 (DMSO) 中进行了溶液研究，其中氯离子主要与铜配位，其中氯离子被铜配位层中的溶剂分子取代。电子光谱和冷冻溶液 EPR 也证实了存在于 MeCN 和 DMSO 中的物种的不同性质。这项工作揭示了有关含酚配体的金属化合物（例如