(E)-N'-(2,4-dihydroxybenzylidene)-4-hydroxybenzohydrazide | 116919-21-2

• 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: (E)-N'-(2,4-dihydroxybenzylidene)-4-hydroxybenzohydrazide
• 英文别名: 4-hydroxy-N’-[(E)-(2,4-dihydroxyphenyl)methylidene]benzohydrazide；2,4-dihydroxy-N'-(4-hydroxybenzylidene)benzohydrazide；4-Hydroxybenzoic (2,4-dihydroxybenzylidene)hydrazide；N-[(E)-(2,4-dihydroxyphenyl)methylideneamino]-4-hydroxybenzamide
• CAS: 116919-21-2
• 化学式: C₁₄H₁₂N₂O₄
• 分子量: 272.26
• InChiKey: AXKPKYGJWCOLJW-OVCLIPMQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  102
• 氢给体数：
  4
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (E)-N'-(2,4-dihydroxybenzylidene)-4-hydroxybenzohydrazide 、 fac-bis(acetonitrile)bromotricarbonylrhenium(I) 以 甲醇 为溶剂， 以53%的产率得到[ReBr(CO)3(2,4-dihydroxy-N'-(4-hydroxybenzylidene)benzohydrazide)]
  参考文献：
  名称：

  Synthesis, spectral studies, crystal structures and TDDFT studies of the rhenium(I) complexes of 2,4-dihydroxy-N′-(4-hydroxybenzilidene) benzohydrazide

  摘要：

  The rhenium(I) carbonyl bromide complex, [ReBr(CO)(3)(HL)], of the ligand derived from 2,4-dihydroxybenzaldehyde and 4-hydroxybenzoic acid hydrazide (HL), has been prepared. HL and its complex have been characterized by elemental analysis, MS, IR, UV-Vis and (1)H NMR spectroscopic methods. The structure of HL and the aqua-complex [Re(OH(2))(CO)(3)(L)] where the ligands are monodeprotonated have been elucidated by X-ray diffraction. The structure of [ReBr(CO)(3)(HL)] has been calculated from conformational parameters found in the aqua-complex. DFT and TDDFT calculations have been performed to obtain the IR spectra and UV-Vis absorption and emission spectra. The calculated spectra agree with the experimental results. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.poly.2010.12.038
• 作为产物：
  描述：

  4-羟基苯甲酰肼 、 2,4-二羟基苯甲醛 在 溶剂黄146 作用下， 以 甲醇 为溶剂， 反应 2.0h， 以90%的产率得到(E)-N'-(2,4-dihydroxybenzylidene)-4-hydroxybenzohydrazide
  参考文献：
  名称：

  栓菌漆酶抑制剂酰肼-腙的合成及构效关系研究

  摘要：

  筛选了一系列酰肼-腙 1-3，即带有苯环的酰肼和醛的亚胺衍生物，作为杂色栓菌漆酶的抑制剂。漆酶是一种含铜酶，抑制它可能会阻止或降低在各种生化过程中产生它的植物病原体的活性。进行了动力学和分子模型研究，并对选定的化合物的对接结果进行了讨论。七种 4-羟基苯甲酰肼 (4-HBAH) 衍生物表现出微摩尔活性 Ki = 24–674 µM，具有预期的和理想的竞争性抑制类型。构效关系（SAR）分析表明，细长的水杨醛框架对于稳定底物对接位点附近的分子具有关键作用。此外，水杨醛片段中3位上苯基和大叔丁基取代基的存在有利于与漆酶中的底物结合袋发生强相互作用。有趣的是，含有较大 3-叔丁基-5-甲基-或 3,5-二叔丁基-2-羟基-亚苄基单元的 3- 和 4-HBAH 衍生物均不与漆酶的活性位点结合，分别充当非竞争性 (Ki = 32.0 µM) 或非竞争性 (Ki = 17.9 µM) 抑制剂。在容易获得

  DOI：

  10.3390/molecules25051255

文献信息

• Design, synthesis and in vitro antimalarial activity of an acylhydrazone library
  作者：Patricia Melnyk、Virginie Leroux、Christian Sergheraert、Philippe Grellier

  DOI：10.1016/j.bmcl.2005.09.058

  日期：2006.1

  A library of acylhydrazone iron chelators was synthesized and tested for its ability to inhibit the growth of a chloroquine-resistant strain of Plasmodium falciparum. Some of these new compounds are significantly more active than desferrioxamine DFO, the iron chelator in widespread clinical use and also than the most effective chelators. (c) 2005 Elsevier Ltd. All rights reserved.
• Synthesis and Structure-Activity Relationship Studies of Hydrazide-Hydrazones as Inhibitors of Laccase from Trametes versicolor
  作者：Halina Maniak、Michał Talma、Konrad Matyja、Anna Trusek、Mirosław Giurg

  DOI：10.3390/molecules25051255

  日期：——

  with the predicted and desirable competitive type of inhibition. The structure–activity relationship (SAR) analysis revealed that a slim salicylic aldehyde framework had a pivotal role in stabilization of the molecules near the substrate docking site. Furthermore, the presence of phenyl and bulky tert-butyl substituents in position 3 in salicylic aldehyde fragment favored strong interaction with the

  筛选了一系列酰肼-腙 1-3，即带有苯环的酰肼和醛的亚胺衍生物，作为杂色栓菌漆酶的抑制剂。漆酶是一种含铜酶，抑制它可能会阻止或降低在各种生化过程中产生它的植物病原体的活性。进行了动力学和分子模型研究，并对选定的化合物的对接结果进行了讨论。七种 4-羟基苯甲酰肼 (4-HBAH) 衍生物表现出微摩尔活性 Ki = 24–674 µM，具有预期的和理想的竞争性抑制类型。构效关系（SAR）分析表明，细长的水杨醛框架对于稳定底物对接位点附近的分子具有关键作用。此外，水杨醛片段中3位上苯基和大叔丁基取代基的存在有利于与漆酶中的底物结合袋发生强相互作用。有趣的是，含有较大 3-叔丁基-5-甲基-或 3,5-二叔丁基-2-羟基-亚苄基单元的 3- 和 4-HBAH 衍生物均不与漆酶的活性位点结合，分别充当非竞争性 (Ki = 32.0 µM) 或非竞争性 (Ki = 17.9 µM) 抑制剂。在容易获得
• Synthesis, spectral studies, crystal structures and TDDFT studies of the rhenium(I) complexes of 2,4-dihydroxy-N′-(4-hydroxybenzilidene) benzohydrazide
  作者：Marta Sánchez-Lozano、Ezequiel M. Vázquez-López、José M. Hermida-Ramón、Carlos M. Estévez

  DOI：10.1016/j.poly.2010.12.038

  日期：2011.4

  The rhenium(I) carbonyl bromide complex, [ReBr(CO)(3)(HL)], of the ligand derived from 2,4-dihydroxybenzaldehyde and 4-hydroxybenzoic acid hydrazide (HL), has been prepared. HL and its complex have been characterized by elemental analysis, MS, IR, UV-Vis and (1)H NMR spectroscopic methods. The structure of HL and the aqua-complex [Re(OH(2))(CO)(3)(L)] where the ligands are monodeprotonated have been elucidated by X-ray diffraction. The structure of [ReBr(CO)(3)(HL)] has been calculated from conformational parameters found in the aqua-complex. DFT and TDDFT calculations have been performed to obtain the IR spectra and UV-Vis absorption and emission spectra. The calculated spectra agree with the experimental results. (C) 2011 Elsevier Ltd. All rights reserved.