N′-(2,4-dihydroxyphenylmethylidene)-3-pyridincarbohydrazide | 303774-56-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: N′-(2,4-dihydroxyphenylmethylidene)-3-pyridincarbohydrazide
• 英文别名: 2,4-dihydroxybenzaldehyde nicotinoylhydrazone；N'-(2,3-dihydroxy-phenylmethylidene)-3-pyridinecarbohydrazide；N’-(2,4-dihydroxy-phenylmethylidene)-3-pyridinecarbohydrazide；nicotinic acid (2,4-dihydroxy-benzylidene)-hydrazide；N'-(2,4-dihydroxybenzylidene)nicotinohydrazide；N-[(2,4-dihydroxyphenyl)methylideneamino]pyridine-3-carboxamide
• CAS: 303774-56-3
• 化学式: C₁₃H₁₁N₃O₃
• 分子量: 257.249
• InChiKey: YKUFPSNDHXRMFP-UHFFFAOYSA-N

物化性质

• 熔点：
  277-278 °C
• 密度：
  1.34±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 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：
  94.8
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  copper(II) choride dihydrate 、 N′-(2,4-dihydroxyphenylmethylidene)-3-pyridincarbohydrazide 以 甲醇 为溶剂， 生成
  参考文献：
  名称：

  芳酰腙的铜（II）配合物：制备和结构表征

  摘要：

  摘要 利用红外(IR)和拉曼光谱分析了苯环上不同取代基的烟酸酰肼和水杨醛衍生物得到的芳酰腙固体铜配合物的结构。研究的芳香腙作为中性、单阴离子或双阴离子三齿配体，取决于络合过程中采用的互变异构体形式。水杨醛环上的各种附加取代基不参与金属配位，因此羰基/烯醇氧、偶氮甲碱氮和酚羟基的氧被提议作为铜（II）离子的配位位点。在所有应用的合成条件下，Cu(II)/腙摩尔比为 1/1 得到 Cu(II) 配合物，但带有硝基的腙除外，无论合成条件如何，它都不会与 Cu(II) 形成络合物。振动光谱表明，腙在双 CN 键上仅具有邻羟基基团，而腙在苯环的对位上具有额外的 OH 基团，形成了以水为配体的单体铜 (II) 配合物，而腙与间位取代基（Cl、OCH3）形成双核铜配合物，其中两个铜（II）离子通过酚氧原子桥接腙分子。通过热重分析研究了制备的铜 (II) 配合物的热性能。振动光谱表明，腙在双 CN 键上仅

  DOI：

  10.1016/j.molstruc.2020.127783
• 作为产物：
  描述：

  烟酸乙酯 在 一水合肼 作用下， 以 乙醇 为溶剂， 反应 4.0h， 生成 N′-(2,4-dihydroxyphenylmethylidene)-3-pyridincarbohydrazide
  参考文献：
  名称：

  酰肼席夫碱：DPPH自由基和超氧阴离子清除剂。

  摘要：

  评估酰肼席夫碱1-27的体外DPPH自由基和超氧阴离子清除活性。他们显示出不同程度的DPPH自由基清除活性，IC（50）值在31.25-473.59 µM之间。化合物8、2和10的IC（50）值分别为31.25±1.32、34.40±0.66和37.24±0.4 µM。标准没食子酸正丙酯显示IC（50）值为30.12±0.27 µM。酰肼1-27表现出体外超氧阴离子清除活性，IC（50）值在175.6-450.89 µM范围内。结果表明，酰肼8、2和10具有DPPH清除活性，与标准的没食子酸正丙酯相当，而酰肼1-27的清除超氧阴离子的活性低于标准的没食子酸正丙酯（IC（50）= 106.34 ±1.6 µM）。

  DOI：

  10.2174/157340612801216111

文献信息

• Acid–Base Properties and Kinetics of Hydrolysis of Aroylhydrazones Derived from Nicotinic Acid Hydrazide
  作者：T. Benković、D. Kontrec、V. Tomišić、A. Budimir、N. Galić

  DOI：10.1007/s10953-016-0504-8

  日期：2016.8

  synthesized from nicotinic acid hydrazide and differently substituted benzaldehydes. The protonation constants of the 12 resulting hydrazones, as well as of the starting compounds, were determined in methanol/water 1/1 mixtures by spectrophotometric–potentiometric batch titrations. In order to determine the effect of substituents on the stability of the C=N bond, the kinetics of hydrolysis of hydrazones was

  摘要 以烟酸酰肼和不同取代的苯甲醛为原料合成了一系列芳酰腙。在甲醇/水 1/1 混合物中通过分光光度法-电位分批滴定法测定 12 个所得腙以及起始化合物的质子化常数。为了确定取代基对 C=N 键稳定性的影响，在酸性和碱性介质中用分光光度法研究腙的水解动力学。HPLC 方法用于研究所选化合物的水解，观察到水解和缩合反应之间的平衡。根据色谱和分光光度数据计算得出的观察到的速率常数非常一致。电喷雾质谱法用于测定反应产物。对于 2,3- 和 2,5- 二羟基取代的苯甲醛衍生物，在碱性介质中观察到氧化和醌的形成。另一方面，与 N'-salicylidene-3-pyridinecarbohydrazide 相比，2,4-二羟基衍生物表现出更高的稳定性。
• Effective methods for the synthesis of hydrazones, quinazolines, and Schiff bases: reaction monitoring using a chemometric approach
  作者：Jana Pisk、Ivica Đilović、Tomica Hrenar、Danijela Cvijanović、Gordana Pavlović、Višnja Vrdoljak

  DOI：10.1039/d0ra06845d

  日期：——

  choice for the quinazolines, while the solid-state melt reaction is more efficient for derivatives of (iso)nicotinic based hydrazones. Crystalline amine-functionalised hydrazones 4a and 4b undergo post-synthetic modifications in reactions with 3- or 4-pyridinecarbaldehyde vapours to form hydrazone-Schiff bases 4a-3py, 4b-3py, 4a-4py, and 4b-4py. Mechanochemical and vapour-mediated reactions are followed

  通过结合合适的醛（2,3- 或 2,4-）可合成腙（ 1a–4a和1b–4b ）、喹唑啉（ 3c·MeOH和3d·MeOH ）和腙-席夫碱（ 4c和4d ）二羟基苯甲醛）与四种酰肼（异烟碱、烟碱和2-或4-氨基苯甲酸酰肼）。描述了一系列制备方法：基于溶液的合成、机械合成和固态熔融反应。对于喹唑啉来说，机械化学方法通常是更好的选择，而对于（异）烟碱基腙的衍生物，固态熔融反应则更有效。结晶胺官能化腙4a和4b在与 3- 或 4-吡啶甲醛蒸气反应中进行合成后修饰，形成腙-席夫碱4a-3py 、 4b-3py 、 4a-4py和4b-4py 。机械化学和蒸汽介导反应之后分别采用异位粉末 X 射线衍射和 IR-ATR 方法。使用主成分分析对这些数据进行化学计量分析，可以深入了解反应曲线和反应时间。由醛和肼获得的吖嗪（ 5a和5b ）会随着温度变化而可逆地改变颜色。所有产品的结构均通过光谱和X射线衍射
• Search for new antimicrobials: spectroscopic, spectrometric, and in vitro antimicrobial activity investigation of Ga(III) and Fe(III) complexes with aroylhydrazones
  作者：David Klarić、Marijana Pocrnić、Dražen Lež、Saša Polović、Darko Kontrec、Ivan Kosalec、Ana Budimir、Nives Galić

  DOI：10.1007/s00775-022-01967-y

  日期：——

  Gram-negative strain of Escherichia coli, and a yeast Candida albicans were investigated. Fe(III)-complexes do not possess antimicrobial activity against all tested strains at concentrations up to 10 mg mL–1. Ga(III) complexes with dihydroxy derivatives showed selective activity, while the broadest range of antibacterial and antifungal activities was observed for complex with 2-hydroxy-3-methoxy-derivative, ligand

  Fe(III) 和 Ga(III) 与N '-(2,3-dihydroxy-phenylmethylidene)-3-pyridinecarbohydrazide ( H 2 L 1 ), N '-(2,4-dihydroxy- ) 配合物的体外抗菌活性苯基-亚甲基)-3-吡啶碳酰肼( H 2 L 2 ), N '-(2,5-二羟基-苯基亚甲基)-3-吡啶碳酰肼( H 2 L 3 ), N '-(2-羟基-3-甲氧基苯基- ) methylidene)-3-pyridine-carbohydrazide ( H 2 L 4 ), N '-(2-hydroxy-4-methoxyphenylmethyl-idene)-3-pyridine-carbohydrazide ( H2 L 5 ), 和N '-(2-hydroxy-5-methoxyphenylmethylidene)-3-pyridinecarbo-hydrazide
• Aluminum(III) complexes of aroylhydrazones derived from nicotinic acid hydrazide: MS, UV-Vis and DFT study
  作者：David Klarić、Viktor Pilepić、Darko Kontrec、Ana Budimir、Nives Galić

  DOI：10.1080/00958972.2023.2300057

  日期：2024.4.17

  In the continuation of our study on aroylhydrazones, the binding properties of N'-(2,3-dihydroxy-phenylmethylidene)-3-pyridinecarbohydrazide (H2L1), N'-(2,4-dihydroxy-phenylmethylidene)-3-pyridinec...

  在我们对芳酰腙的继续研究中，我们研究了 N'-(2,3-二羟基苯基亚甲基)-3-吡啶碳酰肼 (H2L1)、N'-(2,4-二羟基苯基亚甲基)-3-吡啶的结合特性。 ..
• Discovering Potent Inhibitors Against the β-Hydroxyacyl-Acyl Carrier Protein Dehydratase (FabZ) of <i>Helicobacter pylori</i>: Structure-Based Design, Synthesis, Bioassay, and Crystal Structure Determination
  作者：Lingyan He、Liang Zhang、Xiaofeng Liu、Xianghua Li、Mingyue Zheng、Honglin Li、Kunqian Yu、Kaixian Chen、Xu Shen、Hualiang Jiang、Hong Liu

  DOI：10.1021/jm8015602

  日期：2009.4.23

  The discovery of HpFabZ inhibitors is now of special interest in the treatment of various gastric diseases. In this work, three series of derivatives (compounds 3, 4, and 5) were designed, synthesized, and their biological activities were investigated as potential HpFabZ inhibitors in a two phased manner. First, we designed and synthesized two series of derivatives (3a-r and 4a-u) and evaluated the enzyme-based assay against HpFabZ. Five compounds (3i-k, 3m, and 3q) showed potential inhibitory activity, with IC(50) values less than 2 muM. Second, a focused combinatorial library containing 280 molecules was designed employing the LD1.0 program. Twelve compounds (5a-l) were selected and synthesized. The activity of the most potent compound 5h (IC(50) = 0.86 muM) was 46 times higher than that of the hit 1. The high hit rate and the potency of the new HpFabZ inhibitors demonstrated the efficiency of the strategy for the focused library design and virtual screening.