N'-(5-chloro-2-oxoindolin-3-ylidene)isonicotinohydrazide | 1334814-12-8

• 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: N'-(5-chloro-2-oxoindolin-3-ylidene)isonicotinohydrazide
• 英文别名: (Z)-N'-(5-chloro-2-oxoindolin-3-ylidene)isonicotinohydrazide
• CAS: 1334814-12-8；401797-21-5
• 化学式: C₁₄H₉ClN₄O₂
• mdl: MFCD00955242
• 分子量: 300.704
• InChiKey: PVWPHMHEVWFDII-UHFFFAOYSA-N

物化性质

• 密度：
  1.54±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.82
• 重原子数：
  21.0
• 可旋转键数：
  2.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  83.45
• 氢给体数：
  2.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  N'-(5-chloro-2-oxoindolin-3-ylidene)isonicotinohydrazide 在 硫酸 作用下， 生成 8'-chloro-3'-(pyridin-4-yl)[1',3',4'oxadiazino6,5-b]indole
  参考文献：
  名称：

  Design, synthesis and biological evaluation of novel isoniazid hybrids

  摘要：

  DOI：

  10.1016/j.jics.2021.100273
• 作为产物：
  描述：

  异烟肼 、 5-氯靛红 在 溶剂黄146 作用下， 以 乙醇 为溶剂， 反应 0.08h， 以74%的产率得到N'-(5-chloro-2-oxoindolin-3-ylidene)isonicotinohydrazide
  参考文献：
  名称：

  Schiff Bases of Indoline-2,3-dione: Potential Novel Inhibitors of Mycobacterium Tuberculosis (Mtb) DNA Gyrase

  摘要：

  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。

  DOI：

  10.3390/molecules16097864

文献信息

• Isatin derivatives and their use in therapy
  申请人：King Saud University

  公开号：EP2604600A1

  公开（公告）日：2013-06-19

  The present invention relates to compounds of formula (I) wherein R is pyridyl, R1 is selected from Cl or NO2 and R2 is H; or R is 2-nitrofuranosyl, R1 is selected from H, F, Cl, CH3 or OCF3 and R2 is selected from H, phenyl or benzyl; associated pharmaceutical compositions and use of the compounds or compositions in therapy, in particular for the treatment of tuberculosis as well as a method for their preparation.

  本发明涉及式(I)的化合物，其中R为吡啶基，R1选自Cl或NO2，R2为H；或R为2-硝基呋喃基，R1选自H、F、Cl、CH3或OCF3，R2选自H、苯基或苄基；以及相关的药物组合物和将该化合物或组合物用于治疗，特别是用于结核病治疗的方法以及它们的制备方法。
• Gatifloxacin derivatives: Synthesis, antimycobacterial activities, and inhibition of Mycobacterium tuberculosis DNA gyrase
  作者：Dharmarajan Sriram、Alexandra Aubry、Perumal Yogeeswari、L.M. Fisher

  DOI：10.1016/j.bmcl.2006.02.065

  日期：2006.6

  Sixteen 7-substituted gatifloxacin derivatives were synthesized and evaluated for antimycobacterial activity in vitro and in vivo against Mycobacterium tuberculosis H37Rv (MTB) and multi-drug resistant M. tuberculosis (MDR-TB), and also tested for the ability to inhibit the supercoiling activity of DNA gyrase from M. tuberculosis. Among the synthesized compounds, 1-cyclopropyl-6-fluoro-8-methoxy-7-[[[N-4-[I'-(5-isatinyl-beta-semicarbazo)]methyl]3-methyl]N-1-piperazinyl]-4-oxo-1,4-dihydro-3-quinoline carboxylic acid (3d) was found to be the most active compound in vitro with an MIC of 0.0125 mu g/mL against MTB and MTR-TB. In the in vivo animal model 3d decreased the bacterial load in lung and spleen tissues with 3.62- and 3.76-log 10 protections, respectively. Compound 3d was also found to be equally active as gatifloxacin in the inhibition of the supercoiling activity of wild-type M. tuberculosis DNA gyrase with an IC50 of 3.0 mu g/mL. The results demonstrate the potential and importance of developing new quinolone derivatives against mycobacterial infections. (c) 2006 Elsevier Ltd. All rights reserved.
• 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。
• 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