4-((2-(2,4-dinitrophenyl)hydrazono)methyl)benzene-1,3-diol

• 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-((2-(2,4-dinitrophenyl)hydrazono)methyl)benzene-1,3-diol
• 英文别名: N-(2,4-dinitrophenyl)-N'-(2',4'-dihydroxybenzylidene)hydrazone；2,4-dihydroxybenzaldehyde-2,4-dinitrophenylhydrazone；2-[[(2,4-Dinitrophenyl)hydrazinylidene]methyl]-5-oxoniophenolate；2-[[(2,4-dinitrophenyl)hydrazinylidene]methyl]-5-oxoniophenolate
• 化学式: C₁₃H₁₀N₄O₆
• 分子量: 318.246
• InChiKey: CGIRQHNYEBSMOM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  23
• 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：
  157
• 氢给体数：
  3
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  间苯二酚 在 三氯氧磷 作用下， 以 乙醇 、 水 、 乙腈 为溶剂， 反应 10.5h， 生成 4-((2-(2,4-dinitrophenyl)hydrazono)methyl)benzene-1,3-diol
  参考文献：
  名称：

  2,4-dihydroxy benzaldehyde derived Schiff bases as small molecule Hsp90 inhibitors: Rational identification of a new anticancer lead

  摘要：

  Hsp90 is a molecular chaperone that heals diverse array of biomolecules ranging from multiple oncogenic proteins to the ones responsible for development of resistance to chemotherapeutic agents. Moreover they are over-expressed in cancer cells as a complex with co-chaperones and under-expressed in normal cells as a single free entity. Hence inhibitors of Hsp90 will be more effective and selective in destroying cancer cells with minimum chances of acquiring resistance to them. In continuation of our goal to rationally develop effective small molecule azomethines against Hsp90, we designed few more compounds belonging to the class of 2,4-dihydroxy benzaldehyde derived imines (1-13) with our validated docking protocol. The molecules exhibiting good docking score were synthesized and their structures were confirmed by IR, H-1 NMR and mass spectral analysis. Subsequently, they were evaluated for their potential to suppress Hsp90 ATPase activity by Malachite green assay. The antiproliferative effect of the molecules were examined on PC3 prostate cancer cell lines by adopting 3-(4,5-dimethythiazol-2yl)-2,5-diphenyl tetrazolium bromide (MTT) assay methodology. Finally, schiff base 13 emerged as the lead molecule for future design and development of Hsp90 inhibitors as anticancer agents. (C) 2015 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.bioorg.2015.02.003

文献信息

• Synthesis and antifungal activity of substituted salicylaldehyde hydrazones, hydrazides and sulfohydrazides
  作者：Gregory L. Backes、Donna M. Neumann、Branko S. Jursic

  DOI：10.1016/j.bmc.2014.07.022

  日期：2014.9

  Efficient synthetic procedures for the preparation of acid hydrazines and hydrazides were developed by converting the corresponding carboxylic acid into the methyl ester catalyzed by Amberlyst-15, followed by a reaction with hydrazine monohydrate. Sulfohydrazides were prepared from the corresponding sulfonyl chlorides and hydrazine monohydrate. Both of these group of compounds were condensed with substituted

  通过将相应的羧酸转化成由Amberlyst-15催化的甲酯，然后与一水合肼反应，开发出了用于制备酰肼和酰肼的有效合成方法。磺酰肼由相应的磺酰氯和肼一水合物制备。使用梯度浓缩方法将这两组化合物与取代的水杨醛缩合，生成大量的,、酰肼和磺酰肼类似物库。制备的类似物的抗真菌活性表明，水杨醛hydr和酰肼是有效的真菌生长抑制剂，几乎没有哺乳动物细胞毒性，这使这些类似物成为未来治疗发展的新靶标。
• Synthesis and Antimicrobial Resistant Modulatory Activity of 2,4-Dinitrophenylhydrazone Derivatives as Agents against Some ESKAPE Human Pathogens
  作者：Alberta Ade、Cedric D. K. Amengor、Abena Brobbey、Isaac Ayensu、Benjamin K. Harley、Yaw Duah Boakye

  DOI：10.1155/2020/2720697

  日期：2020.10.7

  A library of six novel phenylhydrazones were synthesized and evaluated for their in vitro antimicrobial and resistance modulating activity against a panel of Gram-positive, Gram-negative, and fungal species. The compounds were produced in good yields of 60–92% w/w and characterized using melting point, UV-visible spectroscopy, infrared, and nuclear magnetic resonance (1H, 13C, and DEPT-Q) techniques. Mass spectroscopy was used to confirm the identity of one of the most active compounds, 5 [SA5]. The phenylhydrazones showed activity against all the six selected microorganisms with minimum inhibitory concentration (MIC) values of the most active compounds, 1 [BP1] and 5 [SA5], at 138 µM (Klebsiella pneumoniae) and 165 µM (Streptococcus pneumoniae), respectively. Compound 1 [BP1] further demonstrated a high resistance modulatory activity at 1.078 µM against Streptococcus pneumoniae and Klebsiella pneumoniae.

  合成了一个包含六种新型苯基肼酮化合物的图书馆，并针对一系列革兰氏阳性、革兰氏阴性和真菌物种评估了它们的体外抗菌和耐药调节活性。这些化合物的产率高，达到60-92%（重量/重量），并使用熔点、紫外-可见光谱、红外和核磁共振（1H、13C和DEPT-Q）技术进行了表征。质谱技术用于确认其中一种最活性化合物5 [SA5] 的身份。苯基肼酮对所有六种选定的微生物表现出活性，其中最活性化合物1 [BP1] 和5 [SA5] 的最小抑制浓度（MIC）值分别为138 µM（肺炎克雷伯菌）和165 µM（肺炎链球菌）。化合物1 [BP1] 进一步表现出对肺炎链球菌和肺炎克雷伯菌的高耐药调节活性，MIC值为1.078 µM。
• 基于腙类衍生物的荧光分子探针及其制备方法和在阳离子识别方面的应用
  申请人：新乡医学院

  公开号：CN110396404B

  公开（公告）日：2022-06-17

  本发明公开了一种基于腙类衍生物的荧光分子探针及其制备方法和在阳离子识别方面的应用，本发明的技术方案要点为：基于腙类衍生物的荧光分子探针的结构式为： 本发明还具体公开了基于腙类衍生物的荧光分子探针的制备方法及其在阳离子识别方面的应用。本发明合成路线合理可行，步骤简单，条件温和，收率较高，且对Cu2+和Fe3+的结合能力较好，因此该系列荧光分子探针在阳离子识别方面具有潜在的应用前景。
• Ahad, Ghulam; Khan, Momin; Khan, Asif, Journal of the Chemical Society of Pakistan, 2018, vol. 40, # 5, p. 961 - 973
  作者：Ahad, Ghulam、Khan, Momin、Khan, Asif、Ibrahim, Mohammad、Salar, Uzma、Kanwal、Khan, Khalid Mohammed、Perveen, Shahnaz

  DOI：——

  日期：——
• Acid-Base Indicator Properties of Synthesized Phenylhydrazones: 4-(2-(2,4-Dinitrophenyl) Hydrazono) Methyl)-2 Methoxy Phenol and 4-(2-(2,4-Dinitrophenylhydrazono) Methyl) Benzene-1,3-diol
  作者：Cedric D. K. Amengor、Abena Brobbey、Isaac Ayensu、Emmanuel Orman、Paul Peprah、Billy Mawunyo Abudey、Seth Junior Ayihi、Claudia Naa Dedei Attoh、Alberta Ade、Paul Kwesi Sodzi、James Sarpong Aboagye

  DOI：10.1155/2022/3667814

  日期：2022.9.20

  4-(2-(2,4-Dinitrophenyl) hydrazone) methyl)-2 methoxy phenol (IND-X) and 4-(2-(2, 4-dinitrophenylhydrazono) methyl) benzene-1,3-diol (IND-Y) were synthesised by condensation reactions with 2,4-dinitrinophenylhydrazine and were observed to possess acid-base indicator properties. The study was conducted to explore and verify their use in different analytical situations and, consequently, validate them. Analysis of their use in acid-base titrations between strong acids/strong bases and weak acids/strong bases as well as pharmaceutical applications in the assay of ibuprofen pure powder and batch of ibuprofen tablets (400 mg) using standard methods in the British Pharmacopoeia (2020) was all considered. The validations were performed by the International Conference on Harmonisation of Technical Requirements for the registration of Pharmaceuticals for Humans Q2 (R1) guidelines. The outcomes were statistically compared with existing conventional analytical approaches. Titrimetric data obtained were analyzed statistically by Student’s t-test and one-way ANOVA at a 95% confidence level. IND-X and IND-Y were shown to be similar in behaviour to phenolphthalein, methyl orange, and methyl red as visual indicators after preliminary evidence of sharp colour changes in acid, alkaline, and neutral pH solutions. The use of the two indicators in the assay of ibuprofen powder and tablets has also been established. The validation parameters considered were found to be consistent with respective acceptance criteria for analytical purposes. IND-X and IND-Y are therefore proposed as alternative acid-base indicators to methyl red, methyl orange, and phenolphthalein for routine volumetric analysis in students’ laboratory experiments. They also serve as alternative indicators to phenolphthalein for the titrimetric analysis of ibuprofen-based samples and products.