N'-[(4-chlorophenyl)methylidene]-2-hydroxybenzohydrazide | 18176-37-9

• 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-chlorophenyl)methylidene]-2-hydroxybenzohydrazide
• 英文别名: 2-hydroxybenzoic acid (4-chlorobenzylidene)hydrazide；N'-(4-chlorobenzylidene)-2-hydroxybenzohydrazide；N-(4-chlorobenylidene)-2-hydroxbenzohydrazide；salicylic acid-(4-chloro-benzylidenehydrazide)；Salicylsaeure-(4-chlor-benzylidenhydrazid)；4-Chlor-benzaldehyd-salicyloylhydrazon；N-[(4-chlorophenyl)methylideneamino]-2-hydroxybenzamide
• CAS: 18176-37-9
• 化学式: C₁₄H₁₁ClN₂O₂
• 分子量: 274.707
• InChiKey: HNHWDPXSZPBROS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 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：
  61.7
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N'-[(4-chlorophenyl)methylidene]-2-hydroxybenzohydrazide 反应 1.0h， 生成 3-N-acetyl-5-[2-acetoxyphenyl]-2-(4-chlorophenyl)-2,3-dihydro-1,3,4-oxadiazole
  参考文献：
  名称：

  Formation of 1,3,4-oxadiazolines and 1,3,4-oxadiazepines through acetylation of salicylic hydrazones

  摘要：

  A new series of 1,3,4-oxadiazolines and 1,3,4-oxadiazepines are prepared in a one-step reaction through cyclization of various N-benzylidene-2-hydroxybenzohydrazides. Cyclization in acetic anhydride yielded 1,3,4-oxadiazolines, while the reaction carried out in acetic anhydride-acetic acid gave 1,3,4-oxadiazepines, in some cases. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2014.12.037
• 作为产物：
  描述：

  水杨酸甲酯 在 一水合肼 、 溶剂黄146 作用下， 以 乙醇 、 水 为溶剂， 反应 15.0h， 生成 N'-[(4-chlorophenyl)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

• Synthesis of some Schiff base Derivatives using One pot Grinding Method and Its Biological activities
  作者：Anusuya V Anusuya V、Muruganantham N Muruganantham N、Anitha P Anitha P、Mahesh S Mahesh S

  DOI：10.13005/ojc/380626

  日期：2022.12.30

  In this present study, we reported the synthesis of some Schiff base derivatives by one pot grinding method from 2-hydroxy benzohydrazide and Aromatic aldehydes. NMR and IR spectroscopy were used to characterize the synthesized compounds. The antioxidant, antidiabetic and anti-inflammatory properties of the Schiff base derivatives 3(a-j) were studied. Regarding standards, all the compounds demonstrated good biological activity.

  在本研究中，我们报告了用一锅研磨法从 2-hydroxy benzohydrazide 和芳香醛中合成了一些希夫碱衍生物。核磁共振和红外光谱用于表征合成的化合物。研究了希夫碱衍生物 3（a-j）的抗氧化、抗糖尿病和抗炎特性。根据标准，所有化合物都具有良好的生物活性。
• 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.
• Anusuya; Sujatha; Balaji, European Journal of Molecular and Clinical Medicine, 2020, vol. 7, # 9, p. 1760 - 1769
  作者：Anusuya、Sujatha、Balaji

  DOI：——

  日期：——
• NOVEL METHODS FOR THE PREPARATION OF BENZISOTHIAZOLONES. 2-BENZALAMINOBENZISOTHIAZOLONES
  作者：LEON KATZ、WILLIAM SCHROEDER

  DOI：10.1021/jo01366a017

  日期：1954.1