(Z)-N'-(5-nitro-2-oxoindolin-3-ylidene)isonicotinohydrazide | 81253-07-8

• 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: (Z)-N'-(5-nitro-2-oxoindolin-3-ylidene)isonicotinohydrazide
• CAS: 81253-07-8
• 化学式: C₁₄H₉N₅O₄
• mdl: MFCD00400127
• 分子量: 311.257
• InChiKey: JOGFBVRXQFAJBA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.08
• 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：
  126.59
• 氢给体数：
  2.0
• 氢受体数：
  6.0

反应信息

• 作为产物：
  描述：

  异烟肼 、 5-硝基靛红 以 乙醇 为溶剂， 以34%的产率得到(Z)-N'-(5-nitro-2-oxoindolin-3-ylidene)isonicotinohydrazide
  参考文献：
  名称：

  Synthesis and biological activity of isonicotinoylhydrazones of certain di- and tricarbonyl compounds

  摘要：

  DOI：

  10.1007/bf00761608

文献信息

• Schiff Bases of Indoline-2,3-dione: Potential Novel Inhibitors of Mycobacterium Tuberculosis (Mtb) DNA Gyrase
  作者：Tarek Aboul-Fadl、Hatem A. Abdel-Aziz、Mohammed K. Abdel-Hamid、Tilal Elsaman、Jane Thanassi、Michael J. Pucci

  DOI：10.3390/molecules16097864

  日期：——

  In the present study a series of Schiff bases of indoline-2,3-dione were synthesized and investigated for their Mtb gyrase inhibitory activity. Promising inhibitory activity was demonstrated with some of these derivatives, which exhibited IC50 values ranging from 50–157 mM. The orientation and the ligand-receptor interactions of such molecules within the Mtb DNA gyrase A subunit active site were investigated applying a multi-step docking protocol using Molecular Operating Environment (MOE) and Autodock4 docking software. The results revealed the importance of the isatin moiety and the connecting side chain for strong interactions with the enzyme active site. Among the tested compounds the terminal aromatic ring benzofuran showed the best activity. Promising new leads for developing a novel class of Mtb gyrase inhibitors were obtained from Schiff bases of indoline-2,3-dione.

  在本研究中，合成了一系列吲哚啉-2,3-二酮的施夫碱，并研究了它们对结核分枝杆菌（Mtb）拓扑异构酶抑制活性。其中一些衍生物显示出良好的抑制活性，IC50值范围为50–157 mM。通过采用多步骤的对接方案，利用分子操作环境（MOE）和Autodock4对接软件，研究了这些分子在Mtb DNA拓扑异构酶A亚基活性位点内的取向和配体-受体相互作用。结果揭示了异羧酸基团及连接侧链在与酶活性位点强相互作用中的重要性。在测试的化合物中，末端芳香环苯并呋喃表现出最佳活性。从吲哚啉-2,3-二酮的施夫碱中获得了开发新型Mtb拓扑异构酶抑制剂的有希望的新线索。
• FEDORYAK, S. D.;PRISYAZHNYUK, P. V.;SIDORCHUK, I. I., XIM.-FARMATS. ZH., 1982, 16, N 1, 48-50
  作者：FEDORYAK, S. D.、PRISYAZHNYUK, P. V.、SIDORCHUK, I. I.

  DOI：——

  日期：——
• Design, synthesis and biological evaluation of novel isoniazid hybrids
  作者：R. Nalini、S.M. Basavarajaiah、G.Y. Nagesh、K. Ramakrishna Reddy

  DOI：10.1016/j.jics.2021.100273

  日期：2022.1
• Synthesis and biological activity of isonicotinoylhydrazones of certain di- and tricarbonyl compounds
  作者：S. D. Fedoryak、P. V. Prisyazhnyuk、I. I. Sidorchuk

  DOI：10.1007/bf00761608

  日期：1982.1