N'-(1-(2-hydroxy-4-methoxyphenyl)ethylidene)benzohydrazide | 114070-33-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: N'-(1-(2-hydroxy-4-methoxyphenyl)ethylidene)benzohydrazide
• 英文别名: 1-(2-hydroxy-4-methoxy-α-methylbenzylidene)-2-benzoylhydrazine；2-hydroxy-4-methoxy-α-methylbenzylidene(benzoyl)hydrazone；2-hydroxy-4-methoxyacetophenone benzoylhydrazone；H2hmab；N-[1-(2-hydroxy-4-methoxyphenyl)ethylideneamino]benzamide
• CAS: 114070-33-6
• 化学式: C₁₆H₁₆N₂O₃
• 分子量: 284.315
• InChiKey: IDZSFRMTGXXASX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  70.9
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N'-(1-(2-hydroxy-4-methoxyphenyl)ethylidene)benzohydrazide 在 碘苯二乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 7.0h， 以94%的产率得到1-(2-benzoyl-4-methoxyphenyl)ethanone
  参考文献：
  名称：

  Synthesis of 1,2-Diacylbenzenes fromo-Hydroxyaryl Ketone Acylhydrazones Using [(Diacetoxy)iodo]benzene

  摘要：

  2′-羟基乙酰苯和2′-羟基丙酰苯肼酮3在室温下使用[(二乙酸氧基)-碘]苯在二氯甲烷中氧化为1,2-二酰基苯4，反应具有合成实用性和高产率。

  DOI：

  10.1055/s-1993-25857
• 作为产物：
  描述：

  苯甲酸甲酯 在 hydrazine hydrate 、 溶剂黄146 作用下， 以 甲醇 、 乙醇 为溶剂， 生成 N'-(1-(2-hydroxy-4-methoxyphenyl)ethylidene)benzohydrazide
  参考文献：
  名称：

  Acetophenone benzoylhydrazones as antioxidant agents: Synthesis, in vitro evaluation and structure-activity relationship studies

  摘要：

  Acetophenone and its analogues are naturally-occurring compounds found in many foods and plants. In this study, a series of acetophenone benzoylhydrazones 5a-o were designed and synthesized as new potential antioxidant agents. Designed molecules contain hydrazone and phenolic hydroxyl moieties which possibly contribute to antioxidant activity. The antioxidant properties of compounds 5a-o in terms of reducing ability and radical-scavenging activity were assessed by using FRAP and DPPH tests, respectively. While the unsubstituted compound 5a had the superior capacity in the FRAP assay, the 2,4-dihydroxyacetophenone analogue 5g was the most potent radical scavenger in the DPPH method. The antioxidant potential of representative compounds 5a and 5g was further confirmed by TEAC and ORAC assays. Cell viability assays revealed that while the promising compounds 5a and 5g had no significant toxicity against HepG2 and NIH3T3 cells, they potently protected HepG2 cells against H2O2 -induced oxidative damage at low concentrations. Furthermore, spectroscopic studies with different biometals demonstrated that 5g was able to interact with Cu2+ to form a 1:1 complex.

  DOI：

  10.1016/j.foodchem.2018.06.083

文献信息

• Oxidation of N-Aroylhydrazones of o-hydroxyaryl ketones withlead(IV)acetate: A facile route to aromatic o-diketones
  作者：Antigoni Kotali、Petros G. Tsoungas

  DOI：10.1016/s0040-4039(00)96497-9

  日期：1987.1

  N-Aroylhydrazones of o-hydroxyaryl ketones are oxidized with lead(IV)acetate to aromatic o-diketones in a synthetically useful reaction.

  在合成上有用的反应中，用乙酸铅（IV）将邻羟基芳基酮的N-芳酰基hydr氧化为芳族邻二酮。
• Synthesis, fluorescence study and biological evaluation of three Zn(II) complexes with Paeonol Schiff base
  作者：Dong-dong Qin、Zheng-yin Yang、Gao-fei Qi

  DOI：10.1016/j.saa.2009.06.037

  日期：2009.10

  synthesis of three Paeonol Schiff base ligand and their Zn(II) complexes are reported. The complexes were fully characterized by IR, (1)H NMR, elemental analysis and molar conductivity. The experiment results show the three Zn(II) complexes can emit bright fluorescence at room temperature in DMF solution and solid state. The fluorescence quantum yields (Phi) of three Schiff base ligands and their Zn(II) complexes

  报道了三种丹皮酚席夫碱配体及其锌（II）配合物的合成。通过IR，（1）H NMR，元素分析和摩尔电导率充分表征了该配合物。实验结果表明，三种Zn（II）配合物在DMF溶液和固态下均能在室温下发出明亮的荧光。使用硫酸奎宁作为参比，在1.0N硫酸中的已知0.546的Phi P，计算了三个席夫碱配体及其Zn（II）配合物的荧光量子产率（Phi）。此外，为了开发这些Zn（II）配合物的生物学价值，评估了其对羟基自由基（OH *）的抗氧化活性。结果表明这三种配合物具有优异的清除羟基自由基的能力。
• Synthesis and characterization of Mo(VI) complexes derived from ONO donor acylhydrazones
  作者：Nancy Mathew、M.R. Prathapachandra Kurup

  DOI：10.1016/j.saa.2011.01.021

  日期：2011.5

  Four new dioxomolybdenum(VI) complexes were prepared using different acylhydrazones. Hydrazones used for complexation were derived from 2-hydroxy-4-methoxybenzaldehyde, 2-hydroxy-4-methoxyacetophenone, benzhydrazide and nicotinoyl hydrazide. The complexes were characterized by various spectroscopic techniques, thermal and elemental analyses. The (1)H NMR and IR spectral data indicate tridentate nature of the ligands through enolization. IR spectra provide information about the dimeric nature of the complexes. The thermal analyses of the complexes showed the presence of lattice water in some of the complexes. (C) 2011 Elsevier B.V. All rights reserved.
• Spectral studies of copper(II) complexes of tridentate acylhydrazone ligands with heterocyclic compounds as coligands: X-ray crystal structure of one acylhydrazone copper(II) complex
  作者：Nancy Mathew、Maheswaran Sithambaresan、M.R. Prathapachandra Kurup

  DOI：10.1016/j.saa.2011.04.036

  日期：2011.9

  Six copper(II) complexes of 2-hydroxy-4-methoxybenzaldehyde nicotinoylhydrazone (H(2)hmbn), 2-hydroxy-4-methoxyacetophenone nicotinoylhydrazone (H(2)hman), 2-hydroxy-4-methoxybenzaldehyde benzoylhydrazone (H(2)hmbb) and 2-hydroxy-4-methoxyacetophenone benzoylhydrazone (H(2)hmab) have been synthesized. The complexes viz. [Cu(hmbn)](2)center dot 2H(2)O (1). [Cu(hman)](2) (2), [Cu(hmbb)](2)center dot 2H(2)O (3), [Cu(hmbb)phen]center dot 1(1/2)H2O (4). [Cu(hmbb)(bipy)center dot H2O] (5) and [Cu(hmab)phen] (6) were characterized by different physicochemical techniques. The crystal structure of [Cu(hman)phen] is obtained and it has a distorted square pyramidal geometry with pi-pi stacking interactions and significant C-H pi interactions. (C) 2011 Elsevier B.V. All rights reserved.
• Evaluation of the antioxidant, DNA interaction and tumor cell cytotoxicity activities of Copper(II) complexes with Paeonol Schiff-base
  作者：Dong-Dong Qin、Zheng-Yin Yang、Fu-Hong Zhang、Bo Du、Ping Wang、Tian-Rong Li

  DOI：10.1016/j.inoche.2010.03.030

  日期：2010.6

  Herein, we report for the first time on the preparation of four Paeonol Schiff-base ligands: 1,2-Bis(2-hydroxy-4-methoxy-alpha-methylbenzylideneimino) ethane (H(2)L(1)), 2-hydroxy-4-methoxy-alpha-methylbenzylidene (benzoyl) hydrazone (HL(2)), 2-hydroxy-4-methoxyacetophenone-ethanolamine Schiff-base (HL(3)), and 2-hydroxy-4-methoxyacetophenone(2'-hydroxybenzoyl) hydrazone (H(2)L(4)), and their Cu(II) complexes, of which the structure of C(11)N(2)O(6)H(14)Cu(CuL(3)center dot NO(3)) was confirmed by X-ray diffraction. Antioxidant activities of four Cu(II) complexes were studied by the standard non-enzymatic NBT method and Fenton system, used to produce superoxide anion radicals and hydroxyl radicals, respectively. The results show these Cu(II) complexes have excellent antioxidant activities. DNA-binding and in vitro cytotoxicity experiments were utilized to further investigate the biological activities of C(11)N(2)O(6)H(14)Cu(CuL(3)center dot NO(3)). These results support C(11)N(2)O(6)H(14)Cu as a potential candidate for biological use because it shows not only high antioxidant and moderate DNA-binding activities, but also good tumor cell cytotoxicity activities in human cell lines carcinomas Hep-2 (larynx), for the range of concentrations tested. (C) 2010 Elsevier B.V. All rights reserved.