2-hydroxy-N'-(4-hydroxybenzylidene)benzohydrazide | 87444-15-3

• 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: 2-hydroxy-N'-(4-hydroxybenzylidene)benzohydrazide
• 英文别名: 2-hydroxy-N-[(4-hydroxyphenyl)methylideneamino]benzamide
• CAS: 87444-15-3
• 化学式: C₁₄H₁₂N₂O₃
• mdl: MFCD00430717
• 分子量: 256.261
• InChiKey: QARCGYPQQSPAFJ-UHFFFAOYSA-N

物化性质

• 熔点：
  236-238 °C(Solv: ethanol (64-17-5))
• 密度：
  1.26±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 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：

  2-hydroxy-N'-(4-hydroxybenzylidene)benzohydrazide 、 巯基乙酸 在 溶剂黄146 作用下， 以68%的产率得到2-hydroxy-N-(2-(4-hydroxyphenyl)-4-oxothiazolidin-3-yl)benzamide
  参考文献：
  名称：

  In vitro α-glucosidase and α-amylase inhibitory potential and molecular docking studies of benzohydrazide based imines and thiazolidine-4-one derivatives

  摘要：

  DOI：

  10.1016/j.molstruc.2021.132058
• 作为产物：
  描述：

  水杨酸乙酯 在 hydrazine hydrate 作用下， 以 乙醇 为溶剂， 生成 2-hydroxy-N'-(4-hydroxybenzylidene)benzohydrazide
  参考文献：
  名称：

  In vitro α-glucosidase and α-amylase inhibitory potential and molecular docking studies of benzohydrazide based imines and thiazolidine-4-one derivatives

  摘要：

  DOI：

  10.1016/j.molstruc.2021.132058

文献信息

• 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。
• 10.1016/j.tube.2024.102545
  作者：Ieque, Andressa Lorena、Palomo, Carolina Trevisolli、Gabriela de Freitas Spanhol, Vitória、Fróes da Motta Dacome, Maria Luiza、Júnior do Carmo Pereira, José、Candido, Francielli Cavalcante、Caleffi-Ferracioli, Katiany Rizzieri、Dias Siqueira, Vera Lucia、Cardoso, Rosilene Fressatti、Vandresen, Fábio、Alves-Olher, Vanessa Guimarães、de Lima Scodro, Regiane Bertin

  DOI：10.1016/j.tube.2024.102545

  日期：——

  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.
• Selectively catalytic epoxidation of α-pinene with dry air over the composite catalysts of Co–MOR(L) with Schiff-base ligands
  作者：X.-H. Lu、J. Lei、X.-L. Wei、X.-T. Ma、T.-J. Zhang、W. Hu、D. Zhou、Q.-H. Xia

  DOI：10.1016/j.molcata.2015.02.006

  日期：2015.5

  Twelve bi-/tridentate Schiff-base ligands (L-1-L-12) have been designed, synthesized and coordinated with ion-exchanged Co-MOR (Mordenite) forming a series of Co-MOR(L) composite catalysts, for which various analyzes and characterizations are conducted. Selectively catalytic epoxidation of alpha-pinene with dry air over Co-MOR(L) catalysts has been carried out, where uses TBHP in small amounts as the initiator. Among these Co-MOR(L) catalysts, Co-MOR(L-8) exhibits the best activity for the titled reaction to obtain 85.8 mol% conversion and 90.8% selectivity of epoxide. Some factors such as the structure of ligands, the oxidants, the solvents, the catalyst amount, the reaction temperature and time play important roles in controlling the epoxidation. The recyclable stability of the Co-MOR(L-8) catalyst is confirmed. The studies on the electrochemical behaviors of Co species in Co-MOR(L-8) reveal the importance of reversible change between Co oxidation states for the epoxidation. (C) 2015 Elsevier B.V. All rights reserved.