4-hydroxy-N'-(4-hydroxybenzylidene)benzohydrazide | 100872-56-8

• 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: 4-hydroxy-N'-(4-hydroxybenzylidene)benzohydrazide
• 英文别名: 4-hydroxybenzaldehyde 4-hydroxybenzoyl hydrazone；4-hydroxybenzoic acid (4-hydroxybenzylidene)hydrazide；4-hydroxy-[(4-hydroxyphenyl)methylidene]benzohydrazide；4-Hydroxybenzoic acid (4-hydroxy-benzylidene)-hydrazide；4-hydroxy-N-[(4-hydroxyphenyl)methylideneamino]benzamide
• CAS: 100872-56-8
• 化学式: C₁₄H₁₂N₂O₃
• mdl: MFCD00431598
• 分子量: 256.261
• InChiKey: IRPCZMRRXGHGBY-UHFFFAOYSA-N

物化性质

• 熔点：
  250-252 °C
• 密度：
  1.26±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  19
• 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：
  81.9
• 氢给体数：
  3
• 氢受体数：
  4

安全信息

• 海关编码：
  2928000090

反应信息

• 作为反应物：
  描述：

  4-hydroxy-N'-(4-hydroxybenzylidene)benzohydrazide 在 lithium perchlorate 作用下， 以 乙腈 为溶剂， 反应 3.0h， 以81%的产率得到2,5-双(4-羟基苯基)-1,3,4-噁二唑
  参考文献：
  名称：

  Electrochemical oxidation of aldehyde-N-arylhydrazones into symmetrical-2,5-disubstituted-1,3,4-oxadiazoles

  摘要：

  报道了一种方便、高效的一锅法合成化学和药学上有趣的对称2,5-二取代-1,3,4-噁二唑。该方案涉及在无水的乙腈–氯酸锂中对醛-N-芳基肼进行阳极氧化。在未分隔的电池和铂电极中进行恒电位电解，在常温条件下生成相应的噁二唑，反应机制通过伏安研究进行了推导。反应过程顺利，原子经济性高。

  DOI：

  10.1007/s11164-012-1013-z
• 作为产物：
  描述：

  对羟基苯甲酸甲酯 在 一水合肼 作用下， 以 乙醇 为溶剂， 反应 18.0h， 生成 4-hydroxy-N'-(4-hydroxybenzylidene)benzohydrazide
  参考文献：
  名称：

  一些新型对羟基苯甲酰肼衍生物的合成、抗高血压活性和 3D-QSAR 研究

  摘要：

  p-羟基苯甲酰肼 2 用芳香族/脂肪族醛处理，然后用二硫化碳环化得到化合物 4a-4n。同样，化合物2通过处理取代的异硫氰酸酯然后处理氯乙酸产生相应的化合物6a-6i。通过无创血压测量和有创血压测量方法测定所有测试化合物的抗高血压活性。测试化合物显示出显着的抗高血压活性。完整的化合物进行了 3D-QSAR 研究。通过PHASE程序进行3D-QSAR分析，获得了具有良好预测能力（r2 = 0.98，q2 = 0.74）的统计可靠模型。

  DOI：

  10.1002/ardp.201000008

文献信息

• Electrosynthesis and screening of novel 1,3,4-oxadiazoles as potent and selective antifungal agents
  作者：Sushma Singh、Laxmi Kant Sharma、Apoorv Saraswat、Ibadur R. Siddiqui、Harbans K. Kehri、Rana K. Pal Singh

  DOI：10.1039/c3ra21904f

  日期：——

  The electrochemical oxidation of aldehyde-N-aroylhydrazone has been studied in the presence of NaClO4 as supporting electrolyte in MeOH solution using cyclic voltammetry and controlled potential electrolysis. The results indicate that intramolecular cyclization of aldehyde-N-aroylhydrazone has been successfully performed at a platinum electrode in an undivided cell with good yields of the corresponding 1,3,4-oxadiazoles at ambient conditions. The reaction products were characterized by spectroscopic methods and a mechanism was deduced from voltammetry studies. The antifungal activity of the synthesized compounds was evaluated on Fusarium oxysporum, Alternaria solani, Candida albicans and Aspergillus niger. The results revealed that all the synthesized compounds have significant antifungal activity against the tested fungi. Among the synthesized derivatives 7b, 7d, 7g, 7h, 7i, 7j and 7r were found to be the most effective antifungal compounds.

  在甲醇溶液中，以NaClO4为支持电解质，通过循环伏安法和控制电位电解法研究了醛-N-芳酰腙的电化学氧化反应。结果表明，在室温条件下，在不分隔的铂电极反应池中，醛-N-芳酰腙成功进行了分子内环化反应，得到了较高产率的相应1,3,4-噁二唑类化合物。通过光谱方法对反应产物进行了表征，并从伏安法研究中推导出反应机理。对合成化合物进行了对 Fusarium oxysporum、Alternaria solani、Candida albicans 和 Aspergillus niger 的抗真菌活性评估。结果显示，所有合成化合物对测试的真菌均显示出显著的抗真菌活性。其中，合成衍生物 7b、7d、7g、7h、7i、7j 和 7r 被发现是最高效的抗真菌化合物。
• Inhibition of Xanthine Oxidase by Thiosemicarbazones, Hydrazones and Dithiocarbazates Derived from Hydroxy-Substituted Benzaldehydes
  作者：Maria Leigh、Daniel J. Raines、Carmen E. Castillo、Anne K. Duhme-Klair

  DOI：10.1002/cmdc.201100054

  日期：2011.6.6

  and tested for XOR inhibitory activity. Hydroxy substitution in the para‐position of the benzaldehyde component was found to confer high inhibitory activities. Acyl hydrazones were generally less potent than thiocarbonyl‐containing Schiff bases. Within the thiosemicarbazone series, chloro and cyano substituents in the para‐position of the thiosemicarbazide unit increased activities further, up to potencies

  非嘌呤黄嘌呤氧化还原酶（XOR）抑制剂是嘌呤类似物别嘌呤醇的重要替代品，别嘌呤醇仍然是治疗与血液中尿酸水平升高有关的疾病的最广泛使用的药物。通过将单，二和三羟基苯甲醛与芳族硫代氨基脲，芳基酰肼和二硫代氨基甲酸酯缩合，合成了三组结构相关的席夫碱，表征并测试了其XOR抑制活性。发现苯甲醛成分对位的羟基取代具有较高的抑制活性。酰基的效力一般不如含硫羰基的席夫碱。内的缩氨基硫脲系列，氯和氰基的取代基对在相同的分析条件下测得，硫代氨基脲单元的位置进一步提高了活性，其效力比基准别嘌呤醇的效力高约四倍。为了说明席夫碱直接与酶活性位点上的钼中心结合的潜力，将每个抑制剂系列的一个代表性实例（H 2 L）与一个顺式-二氧钼（VI）单元配位。 ，以及生成的络合物[MoO 2（L）MeOH]的结构表征。然而，随后的稳态动力学研究表明，混合型抑制作用类似于已知在远离Mo中心的酶的底物进入通道内结合的抑制剂所观察到的
• Synthesis, antiplatelet and antithrombotic activities of resveratrol derivatives with NO-donor properties
  作者：Luiz Antonio Dutra、Jéssica Frade O. Guanaes、Nadine Johmann、Maria Elisa Lopes Pires、Chung Man Chin、Sisi Marcondes、Jean Leandro Dos Santos

  DOI：10.1016/j.bmcl.2017.04.007

  日期：2017.6

  described new resveratrol derivatives with nitric oxide (NO) release properties, ability to inhibit platelet aggregation and in vivo antithrombotic effect. Compounds (4a-f) were able to release NO in vitro, at levels ranging from 24.1% to 27.4%. All compounds (2a-f and 4a-f) have exhibited platelet aggregation inhibition using as agonists ADP, collagen and arachidonic acid. The most active compound

  白藜芦醇（RVT）是对心血管系统具有保护作用的二苯乙烯。然而，包括低生物利用度和快速代谢的缺点限制了其功效。在这项工作中，我们描述了具有一氧化氮（NO）释放特性，抑制血小板聚集的能力和体内抗血栓形成作用的新白藜芦醇衍生物。化合物（4a-f）能够在体外释放NO，含量范围为24.1％至27.4％。使用ADP，胶原蛋白和花生四烯酸作为激动剂，所有化合物（2a-f和4a-f）均显示出血小板聚集抑制作用。与乙酰水杨酸（ASA）相比，活性最高的化合物（4f）出血时间减少，最多可保护80％的体内血栓栓塞事件。
• Synthesis and biological activity of hydrazones of o- and p-hydroxybenzoic acids. Spatial structure of 5-Bromo-2-hydroxybenzylidene-4-hydroxybenzohydrazide
  作者：O. A. Nurkenov、Zh. B. Satpaeva、I. A. Schepetkin、A. I. Khlebnikov、K. M. Turdybekov、T. M. Seilkhanov、S. D. Fazylov

  DOI：10.1134/s1070363217100097

  日期：2017.10

  A series of hydrazones based on hydrazides of o- and p-hydroxybenzoic acids have been prepared. N-(5-Bromo-2-hydroxybenzylidene)-4-hydroxybenzohydrazide has been studied by X-ray diffraction analysis; its molecule forms hydrogen bond with a solvating ethanol molecule. Biological activity of the synthesized hydrazones towards cathepsin E and(or) elastase of human neutrophils has been determined.
• Dynamic polymers containing one acylhydrazone linkage and dynamic behavior thereof
  作者：Zizhen Xu、Peng Zhao、Yongming Chen、Guohua Deng

  DOI：10.1016/j.polymer.2013.03.023

  日期：2013.5

  Dynamic polystyrene (d-PS) and poly(n-butyl acrylate) (d-PBA) with an acylhydrazone linkage at each chain center were synthesized by atom transfer radical polymerization (ATRP) of corresponding monomers using a bis-bromoisobutyrate initiator bearing one acylhydrazone bond. Kinetic studies demonstrated that the polymerization followed a first-order mechanism. When treated with trifluoroacetic acid or heated at 120 degrees C in solution, the polymer chains of d-PS and d-PBA were found to be cleaved partially into blocks of half original length, i.e. PS/2 and PBA/2, implying that a dynamic equilibrium of forming and breaking acylhydrazone bond was established. (C) 2013 Elsevier Ltd. All rights reserved.