N’-(5-nitro-2-oxo-1,2-dihydro-indol-3-ylidene)benzohydrazide | 301819-88-5

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: N’-(5-nitro-2-oxo-1,2-dihydro-indol-3-ylidene)benzohydrazide
• 英文别名: N'-[5-nitro-2-oxo-1,2-dihydro-3H-indol-3-ylidene]benzohydrazide；N'-(5-nitro-2-oxoindol-3-yl)benzohydrazide
• CAS: 301819-88-5
• 化学式: C₁₅H₁₀N₄O₄
• mdl: MFCD00991970
• 分子量: 310.269
• InChiKey: GZIFKDXLIGDEFF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.68
• 重原子数：
  23.0
• 可旋转键数：
  3.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  113.7
• 氢给体数：
  2.0
• 氢受体数：
  5.0

反应信息

• 作为产物：
  描述：

  苯甲醛 在 N-氯代丁二酰亚胺 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 3.25h， 生成 N’-(5-nitro-2-oxo-1,2-dihydro-indol-3-ylidene)benzohydrazide
  参考文献：
  名称：

  Facile synthesis of ninhydrin and isatin based hydrazones in water using PEG-OSO3H as a highly efficient and homogeneous polymeric acid-surfactant combined catalyst

  摘要：

  The synthesis of a series of biologically important ninhydrin and isatin based hydrazones has been carried out by refluxing easily synthesized novel N'-(chloro-aryl-methylene)-tert-butylcarbazates with ninhydrin and isatins in the presence of PEG-OSO3H as catalyst in water medium. The dual characteristic of PEG-OSO3H as a Bronsted acid as well as a phase-transfer catalyst is successfully exploited in this synthesis. Reduced reaction time, operational simplicity, excellent yields of the products with high purity, and more importantly, easy recoverability, and reusability of the homogeneous polymeric catalyst make the reaction an attractive, economic, and sustainable green synthetic methodology. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2013.05.105

文献信息

• Bentonite catalyzed solvent-free synthesis of N′-(2-oxoindolin-3-ylidene) benzohydrazide derivatives under microwave irradiation
  作者：Girlyanderson Araújo da Silva、Aleff Cruz de Castro、Rhuan Karlos Santos Mendes、Dayse das Neves Moreira、Graycyellê Rodrigues da Silva Cavalcanti、Maria Gardennia da Fonseca、João Pedro Agra Gomes、Edilson Beserra de Alencar-Filho、Boniek Gontijo Vaz、Gabriel Franco dos Santos、Gesiane da Silva Lima、Fausthon Fred da Silva、Claudio Gabriel Lima-Junior

  DOI：10.1016/j.molstruc.2022.133914

  日期：2022.12

  overcome these obstacles, this work describes a new methodology for the synthesis of a series of N′-(2-oxoindolin-3-ylidene)benzohydrazide derivatives, using bentonite clay as catalysts under microwave irradiation. The methodology was optimized studying the type and loading of the catalyst, solvent, and heating source. The solvent-free reaction in the presence of bentonite as a catalyst was the best experimental

  靛红衍生的席夫碱在药理学上得到了广泛的探索，但其生产仍主要基于有机溶剂下的合成，这使得该过程更加昂贵并导致产生残留物。为了克服这些障碍，这项工作描述了一种在微波辐射下使用膨润土作为催化剂合成一系列 N'-(2-oxoindolin-3-ylidene) 苯并酰肼衍生物的新方法。该方法在研究催化剂、溶剂和热源的类型和负载量方面进行了优化。在膨润土作为催化剂存在下的无溶剂反应是最佳实验条件，该方法应用于几种靛红衍生的底物，分离产物的收率高达 96%，反应时间在 15-60 分钟之间。所有这些结果都与文献中发现的结果相当或更好，但是采用了使用多相催化的环境兼容方法。最后，该催化剂在至少三个循环中显示出可回收性，而产率和反应时间没有显着损失，证明了这种粘土作为一种低成本和更清洁的替代品的适用性。考虑到所研究分子的生物学潜力，进行了初步的分子对接分析以验证它们对 DNA 促旋酶的亲和力，DNA 促旋
• Designing and Synthesis of New Isatin Derivatives as Potential CDK2 Inhibitors
  作者：Przemysław Czeleń、Agnieszka Skotnicka、Beata Szefler

  DOI：10.3390/ijms23148046

  日期：——

  basis for the development of new groups of inhibitors for this class of enzyme. Therefore, in this work, a new group of potential inhibitors of the CDK2 enzyme, utilizing isatin derivatives and substituted benzoylhydrazines, has been designed based on the application of computational chemistry methods, such as docking and molecular dynamics, and their inhibiting ability was assessed. In the cases of the

  肿瘤仍然是主要的死亡原因之一。因此，寻找能够实施有效治疗的新治疗剂是现代药学面临的重大挑战。导致肿瘤疾病发展的重要因素之一是负责调节细胞分裂过程的酶如细胞周期蛋白依赖性激酶的过度表达。大量研究和已开发药物的实例证实，靛红是开发此类酶的新抑制剂组的便利基础。因此，在这项工作中，基于对接和分子动力学等计算化学方法的应用，设计了一组新的 CDK2 酶潜在抑制剂，利用靛红衍生物和取代的苯甲酰肼，并评估其抑制能力。在选定化合物的情况下，开发了一种合成方法，并估计了新合成衍生物的选定物理化学性质。作为已完成项目的一部分，开发了新的化合物，它们是 CDK2 酶的潜在抑制剂。
• Synthesis and biological evaluation of novel isatin-hydrazide conjugates as potential antidiabetic agents
  作者：Rima D. Alharthy、Syeda Bakhtawar Zahra、Noor Fatima、Arooma Tabassum、Saeed Ullah、Sobia Ahsan Halim、Ajmal Khan、Javid Hussain、Ahmed Al-Harrasi、Zahid Shafiq

  DOI：10.1016/j.molstruc.2023.135783

  日期：2023.9

  features resulting in high blood glucose level. This study's objective was to locate substances with possible anti-hyperglycemic effect that block α-glucosidase. For these studies several novel indole-hydrazide conjugates (3a–3r) were synthesized and examined using a variety of spectroscopic methods. Comparing the investigated compounds from the 3a–3r series to the reference medication acarbose 1C50 = 873

  糖尿病是一种严重的代谢紊乱病症，其患病率非常高，并导致其他健康破坏性并发症。胰腺胰岛素抵抗和β-细胞功能障碍是导致高血糖水平的决定性特征。本研究的目的是找到可能具有阻断 α-葡萄糖苷酶的抗高血糖作用的物质。对于这些研究，合成了几种新型吲哚-酰肼偶联物 ( 3a–3r )，并使用各种光谱方法对其进行了检测。将3a–3r系列的研究化合物与参考药物阿卡波糖 1C 50  = 873.34 ± 1.67  µ M 进行比较，所有化合物均表现出对 α-葡萄糖苷酶的有效抑制作用，IC 50值在 0.51–42.91 µ M范围内。 最高抑制作用见于类似物3p和3o，其 IC 50值 分别为 0.51 ± 0.06 和 1.57 ± 0.08 µM 。构效关系表明，这些化合物的 α-葡萄糖苷酶潜力随新型吲哚-酰肼上的各种取代基模式而变化。动力学和对接检测表明，活性化合物很好地适应了 α-葡萄糖苷酶的活性位点，并表现出混合型抑制作用。
• Facile synthesis of ninhydrin and isatin based hydrazones in water using PEG-OSO3H as a highly efficient and homogeneous polymeric acid-surfactant combined catalyst
  作者：Kamalesh Debnath、Sudipta Pathak、Animesh Pramanik

  DOI：10.1016/j.tetlet.2013.05.105

  日期：2013.7

  The synthesis of a series of biologically important ninhydrin and isatin based hydrazones has been carried out by refluxing easily synthesized novel N'-(chloro-aryl-methylene)-tert-butylcarbazates with ninhydrin and isatins in the presence of PEG-OSO3H as catalyst in water medium. The dual characteristic of PEG-OSO3H as a Bronsted acid as well as a phase-transfer catalyst is successfully exploited in this synthesis. Reduced reaction time, operational simplicity, excellent yields of the products with high purity, and more importantly, easy recoverability, and reusability of the homogeneous polymeric catalyst make the reaction an attractive, economic, and sustainable green synthetic methodology. (C) 2013 Elsevier Ltd. All rights reserved.