N'-[(4-methoxyphenyl)methylidene]-2-hydroxybenzohydrazide | 3291-01-8

• 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: N'-[(4-methoxyphenyl)methylidene]-2-hydroxybenzohydrazide
• 英文别名: 2-hydroxy-N'-(4-methoxybenzylidene)benzohydrazide；N'-(4-methoxybenzylidene)-2-hydroxybenzohydrazide；2-hydroxy-N-(4-methoxybenzylidene)benzohydrazide；4-methoxy-benzylidene salicylichydrazide；salicylic acid-(4-methoxy-benzylidenehydrazide)；Salicylsaeure-(4-methoxy-benzylidenhydrazid)；2-hydroxy-N-[(4-methoxyphenyl)methylideneamino]benzamide
• CAS: 3291-01-8
• 化学式: C₁₅H₁₄N₂O₃
• 分子量: 270.288
• InChiKey: UNTUZVVEMVWURQ-UHFFFAOYSA-N

物化性质

• 熔点：
  215-217 °C
• 密度：
  1.19±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  70.9
• 氢给体数：
  2
• 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：

  N'-[(4-methoxyphenyl)methylidene]-2-hydroxybenzohydrazide 在 硫酸 作用下， 以 水 为溶剂， 反应 48.0h， 以83%的产率得到2,3-dihydro-5-(2-hydroxyphenyl)-2-(4-methoxyphenyl)-1,3,4-oxadiazole
  参考文献：
  名称：

  水杨酸肼的某些杂环化合物的合成及生物评价

  摘要：

  从2-羟基苯甲酰肼开始制备了各种杂环化合物；例如，酰肼腙环化3由2- hydroxybenzohydrazide衍生2用乙酸酐或浓硫酸，得到1,3,4-恶二唑衍生物4 - 5。在另一方面，2-羟基苯甲酰肼的环化直接2与一个碳环化剂得到的1,3,4-恶二唑的新衍生7，8，9，10，11。用吡啶中的巯基乙酸对酰肼3进行加热，得到噻唑烷酮12。当2-羟基苯甲酰肼2与脂肪族羧酸（例如甲酸或乙酸）反应时，得到相应的N-甲酰基或N-乙酰基衍生物6。随后在吡啶中使用五硫化二磷对6进行环化，得到1,3,4-噻二唑13。2-羟基苯并肼与乙酰乙酸乙酯的环化反应得到吡唑啉酮衍生物14。最后，当在35％HCl中用硫氰酸铵处理酰肼2的乙醇溶液时，得到硫代氨基脲15。后续治疗15用浓硫酸或10％氢氧化钠溶液分别制得5-氨基-1,3,4-噻二唑16和1,2,4-三唑17。使用1 H NMR，IR光谱和元素分析确认了所有

  DOI：

  10.1002/jhet.2516
• 作为产物：
  描述：

  N'-[2-(4-nitrophenyl)-2-ethylidene]-2-hydroxybenzohydrazide 在 硫酸 、 溶剂黄146 作用下， 以 乙醇 、 水 为溶剂， 生成 N'-[(4-methoxyphenyl)methylidene]-2-hydroxybenzohydrazide
  参考文献：
  名称：

  水杨酸肼的某些杂环化合物的合成及生物评价

  摘要：

  从2-羟基苯甲酰肼开始制备了各种杂环化合物；例如，酰肼腙环化3由2- hydroxybenzohydrazide衍生2用乙酸酐或浓硫酸，得到1,3,4-恶二唑衍生物4 - 5。在另一方面，2-羟基苯甲酰肼的环化直接2与一个碳环化剂得到的1,3,4-恶二唑的新衍生7，8，9，10，11。用吡啶中的巯基乙酸对酰肼3进行加热，得到噻唑烷酮12。当2-羟基苯甲酰肼2与脂肪族羧酸（例如甲酸或乙酸）反应时，得到相应的N-甲酰基或N-乙酰基衍生物6。随后在吡啶中使用五硫化二磷对6进行环化，得到1,3,4-噻二唑13。2-羟基苯并肼与乙酰乙酸乙酯的环化反应得到吡唑啉酮衍生物14。最后，当在35％HCl中用硫氰酸铵处理酰肼2的乙醇溶液时，得到硫代氨基脲15。后续治疗15用浓硫酸或10％氢氧化钠溶液分别制得5-氨基-1,3,4-噻二唑16和1,2,4-三唑17。使用1 H NMR，IR光谱和元素分析确认了所有

  DOI：

  10.1002/jhet.2516

文献信息

• Coordination compounds of hydrazine derivatives with transition metals. XIV. Nickel(II) chelates with bidentate aroylhydrazones and their reactions with heterocyclic bases
  作者：M.F. Iskander、S. Saddeck

  DOI：10.1016/s0020-1693(00)90911-3

  日期：1977.1

  neutral bis(ligand)nickel(II) chelates derived from some bidentate aroylhydrazones have been prepared and characterized. Whatever the solubility permits, the reaction of the neutral bis-(ligand)chelates, NiL 2 , with some heterocyclic bases were studied spectrophotometrically in benzene solution. The stability constants as well as the thermodynamic parameters (ΔG, ΔH, ΔS) for the adduct formation reaction

  摘要制备并表征了由一些双齿芳酰hydr衍生的阳离子和中性双（配体）镍（Ⅱ）螯合物。无论溶解度如何，均在苯溶液中分光光度法研究了中性双（配体）螯合物NiL 2与一些杂环碱的反应。测量了加合物形成反应的稳定性常数以及热力学参数（ΔG，ΔH，ΔS）。已从吡啶溶液中性双（配体）螯合物的结晶中分离出稳定的固态单，双和四吡啶鎓加合物。
• Kinetics of hydrolysis of some N′-(4-substituted benzylidene) salicylohydrazides
  作者：Yassien M. Temerk、Mostafa M. Kamal、Mohamed E. Ahmed

  DOI：10.1039/p29840000337

  日期：——

  The rates of hydrolysis of a series of substituted benzylidenesalicylohydrazide derivatives in 40%(v/v) ethanol–buffer mixture have been investigated by differential pulse polarography. The hydrolysis is catalysed by H+ and its rate follows strictly first-order kinetics. The rate constant decreases with increasing pH up to around pH 3.9, beyond which no measurable reaction was observed; here the protonation

  通过微分脉冲极谱法研究了一系列取代的亚苄基水杨酰肼衍生物在40％（v / v）乙醇-缓冲液混合物中的水解速率。水解由H +催化，其速率严格遵循一级动力学。速率常数随着pH的增加而降低，直至达到3.9左右，超过此值则未观察到可测量的反应。在这里，亚胺的质子化开始明显不完全。水在质子化基质上的侵蚀被认为是决定速率的步骤。报道了pH，分子结构和温度对反应速率和活化能的影响。热力学参数（ΔG ‡，ΔH ‡和ΔS ‡）进行了水解。
• Preclinical tests for salicylhydrazones derivatives to explore their potential for new antituberculosis agents
  作者：Andressa Lorena Ieque、Carolina Trevisolli Palomo、Vitória Gabriela de Freitas Spanhol、Maria Luiza Fróes da Motta Dacome、José Júnior do Carmo Pereira、Francielli Cavalcante Candido、Katiany Rizzieri Caleffi-Ferracioli、Vera Lucia Dias Siqueira、Rosilene Fressatti Cardoso、Fábio Vandresen、Vanessa Guimarães Alves-Olher、Regiane Bertin de Lima Scodro

  DOI：10.1016/j.tube.2024.102545

  日期：2024.9

  This study target the synthesis of 22 salicylhydrazones derivatives to apply screening to explore their potential in the search for new anti-TB prototypes drugs. The minimum inhibitory concentration (MIC) were evaluated against () HRv and clinical isolates. Drug combination assay, cytotoxicity assay, ethidium bromide accumulation assay (EtBr) and analysis regarding the absorption, distribution, metabolism

  本研究的目标是合成 22 种水杨酰腙衍生物，并进行筛选，探索其在寻找新的抗结核原型药物中的潜力。针对 () HRv 和临床分离株评估最低抑菌浓度 (MIC)。还进行了药物组合测定、细胞毒性测定、溴化乙锭累积测定（EtBr）以及吸收、分布、代谢、排泄和毒性（ADMET）和药理特性分析。选择了三种最有希望的化合物（10、11 和 18）进行筛选测试。化合物 18 对 HRv 菌株的 MIC 值最低 (0.49 μg/mL)，其次是化合物 11 (3.9 μg/mL) 和 10 (7.8 μg/mL)。所有化合物均表现出针对药物敏感和耐药临床分离株的活性。所有水杨酰腙的细胞毒性结果都令人鼓舞，化合物 18 的 SI 值高达 4,205。衍生物 10 是唯一一种对单细胞系表现出不乐观的细胞毒性情况的化合物。所有衍生物与异烟肼、乙胺丁醇和利福平联合显示出相加效应（FICI>0.5至4.0）。所有水杨
• Design, synthesis, and evaluation of novel small molecule inhibitors of the influenza virus protein NS1
  作者：Joseph J. Jablonski、Dipwanita Basu、Daniel A. Engel、H. Mario Geysen

  DOI：10.1016/j.bmc.2011.10.026

  日期：2012.1

  Influenza is a continuing world-wide public health problem that causes significant morbidity and mortality during seasonal epidemics and sporadic pandemics. The existing vaccination program is variably effective from year to year, and drug resistance to available antivirals is a growing problem, making the development of additional antivirals an important challenge. Influenza virus non-structural protein 1 (NS1) is the centerpiece of the viral response to the host interferon (IFN) system. NS1 was demonstrated previously to be a potential therapeutic target for antiviral therapy by the identification of specific small-molecule inhibitors. One inhibitory compound, NSC125044, was subjected to chemical evaluation. Initial synthetic work comprised simplifying the core structure by removing unwanted functionality and determination of key features important for activity. Several subclasses of molecules were designed and synthesized to further probe activity and develop the basis for a structure-activity relationship. Apparent potency, as judged by activity in virus replication assays, increased dramatically for some analogs, without cytotoxicity. Results suggest that the target binding site tolerates hydrophobic bulk as well as having a preference for weakly basic substituents. (C) 2011 Elsevier Ltd. All rights reserved.
• 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.