1-methyl-3-[2-(4-nitrophenyl)hydrazono]quinoline-2,4-(1H,3H)-dione | 1111643-34-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 1-methyl-3-[2-(4-nitrophenyl)hydrazono]quinoline-2,4-(1H,3H)-dione
• 英文别名: 1-methyl-3-[(4-nitrophenyl)hydrazinylidene]quinoline-2,4-dione
• CAS: 1111643-34-5
• 化学式: C₁₆H₁₂N₄O₄
• 分子量: 324.296
• InChiKey: XUAQVLICOQTYFM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.22
• 重原子数：
  24.0
• 可旋转键数：
  3.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  104.91
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  1-methyl-3-[2-(4-nitrophenyl)hydrazono]quinoline-2,4-(1H,3H)-dione 、 nickel(II) acetate tetrahydrate 、 N,N-二甲基甲酰胺 以 N,N-二甲基甲酰胺 为溶剂， 反应 5.0h， 以47%的产率得到trans-[Ni(Lb)2(DMF)2]
  参考文献：
  名称：

  两对1：2镍（ii）和铜（ii）金属络合物染料，显示相同的反式构型和偶氮–转变，但热特性不同†

  摘要：

  两对1：2的中性反式单核过渡金属（M = Ni II和Cu II）配合物吡啶-2,4-二酮 和 喹啉-2,4-二酮本文已经在结构和光谱上表征和比较了基于杂环的杂环染料。四种配合物的X射线单晶衍射分析，即反式-[Ni（L a）2（DMF）2 ]（1），反式-[Cu（L a）2（DMF）2 ]（2），反式-[Ni（L b）2（DMF）2 ]（3）和反式-[Cu（L b）2（DMF）2 ]（4），表明它们具有相同的反式双齿螯合双阴离子配体与两个轴向配位的DMF分子之间的构型。此外，由腙到偶氮结构的变换已经观察到两个二齿螯合配位体L一-和L b -后金属离子络合。更重要的是，同时DSC / TG-MS-FTIR方法已用于探索四种中性金属配合物染料1-4的热稳定性，其中Ni II和Cu II配合物中的两个轴向配位的DMF分子表现出明显的分解行为。由于它们不同的M-O键长来自于Jahn-Teller畸变。

  DOI：

  10.1039/c3dt50229e
• 作为产物：
  描述：

  4-羟基-N-甲基-2-喹啉 、 4-硝基苯胺 在 盐酸 、 sodium nitrite 、 sodium acetate 作用下， 以 水 为溶剂， 反应 1.5h， 以43%的产率得到1-methyl-3-[2-(4-nitrophenyl)hydrazono]quinoline-2,4-(1H,3H)-dione
  参考文献：
  名称：

  Synthesis and binary QSAR study of antitubercular quinolylhydrazides

  摘要：

  In continuation with our previous work in anti-TB research area, in the present study we have demonstrated the structural diversity of quinolylhydrazides as potent anti-tuberculars. The compound library was synthesized by molecular hybridization approach and tested in vitro against Mycobacterium tuberculosis H(37)Rv strains. Among the designed conjugates, the most promising molecules were found to exhibit 100% Growth Inhibition (GI) at MIC <6.25 mu g/mL. Moreover, several analogs in the designed series were also turned out as excellent anti-tuberculars. To probe the structural characteristics influencing on the SAR, the classification model was generated using a binary QSAR approach termed recursive partitioning (RP) analysis. The significant features outlined by the RP model act as a guide in order to design the 'lead' compound. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.06.076

文献信息

• Synthesis and binary QSAR study of antitubercular quinolylhydrazides
  作者：Atul Manvar、Vijay Khedkar、Jignesh Patel、Vipul Vora、Narsinh Dodia、Gautam Patel、Evans Coutinho、Anamik Shah

  DOI：10.1016/j.bmcl.2013.06.076

  日期：2013.9

  In continuation with our previous work in anti-TB research area, in the present study we have demonstrated the structural diversity of quinolylhydrazides as potent anti-tuberculars. The compound library was synthesized by molecular hybridization approach and tested in vitro against Mycobacterium tuberculosis H(37)Rv strains. Among the designed conjugates, the most promising molecules were found to exhibit 100% Growth Inhibition (GI) at MIC <6.25 mu g/mL. Moreover, several analogs in the designed series were also turned out as excellent anti-tuberculars. To probe the structural characteristics influencing on the SAR, the classification model was generated using a binary QSAR approach termed recursive partitioning (RP) analysis. The significant features outlined by the RP model act as a guide in order to design the 'lead' compound. (C) 2013 Elsevier Ltd. All rights reserved.
• Two pairs of 1 : 2 nickel(ii) and copper(ii) metal-complex dyes showing the same trans configuration and azo–hydrazone transformation but different thermal properties
  作者：Xiao-Chun Chen、Yin-Ge Wang、Tao Tao、Jiao Geng、Wei Huang、Hui-Fen Qian

  DOI：10.1039/c3dt50229e

  日期：——

  of 1 : 2 neutral trans mononuclear transition-metal (M = NiII and CuII) complexes of pyridine-2,4-dione and quinoline-2,4-dione based heterocyclic dyes have been structurally and spectrally characterized and compared herein. X-ray single-crystal diffraction analyses of four complexes, namely trans-[Ni(La)2(DMF)2] (1), trans-[Cu(La)2(DMF)2] (2), trans-[Ni(Lb)2(DMF)2] (3) and trans-[Cu(Lb)2(DMF)2] (4)

  两对1：2的中性反式单核过渡金属（M = Ni II和Cu II）配合物吡啶-2,4-二酮 和 喹啉-2,4-二酮本文已经在结构和光谱上表征和比较了基于杂环的杂环染料。四种配合物的X射线单晶衍射分析，即反式-[Ni（L a）2（DMF）2 ]（1），反式-[Cu（L a）2（DMF）2 ]（2），反式-[Ni（L b）2（DMF）2 ]（3）和反式-[Cu（L b）2（DMF）2 ]（4），表明它们具有相同的反式双齿螯合双阴离子配体与两个轴向配位的DMF分子之间的构型。此外，由腙到偶氮结构的变换已经观察到两个二齿螯合配位体L一-和L b -后金属离子络合。更重要的是，同时DSC / TG-MS-FTIR方法已用于探索四种中性金属配合物染料1-4的热稳定性，其中Ni II和Cu II配合物中的两个轴向配位的DMF分子表现出明显的分解行为。由于它们不同的M-O键长来自于Jahn-Teller畸变。