2-(4-methoxyphenyl)-4-methyl-1H-pyrrolo[3,4-c]quinoline-1,3(2H)-dione | 687573-09-7

• 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: 2-(4-methoxyphenyl)-4-methyl-1H-pyrrolo[3,4-c]quinoline-1,3(2H)-dione
• 英文别名: 2-(4-Methoxyphenyl)-4-methyl-1H,2H,3H-pyrrolo[3,4-C]quinoline-1,3-dione；2-(4-methoxyphenyl)-4-methylpyrrolo[3,4-c]quinoline-1,3-dione
• CAS: 687573-09-7
• 化学式: C₁₉H₁₄N₂O₃
• mdl: MFCD03829224
• 分子量: 318.332
• InChiKey: UHMFXRALIDEKHA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  24
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  59.5
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  乙酰基乙酰对甲氧基苯胺 、 靛红 在 iron(III) oxide 作用下， 以 甲苯 为溶剂， 反应 6.0h， 以88%的产率得到2-(4-methoxyphenyl)-4-methyl-1H-pyrrolo[3,4-c]quinoline-1,3(2H)-dione
  参考文献：
  名称：

  Sonochemically synthesized ferromagnetic Fe₃O₄nanoparticles as a recyclable catalyst for the preparation of pyrrolo[3,4-c]quinoline-1,3-dione derivatives

  摘要：

  本论文报道了通过超声辐照Fe2O3溶液和紫苏叶提取物绿色、快速合成Fe3O4纳米颗粒的方法，紫苏叶提取物既作为还原剂也作为配位剂。合成的Fe3O4纳米颗粒通过傅里叶变换红外光谱（FT-IR）、X射线衍射（XRD）、透射电子显微镜（TEM）、扫描电子显微镜（SEM）、能量分散X射线分析、振动样品磁力计、热重分析（TGA）和X射线光电子能谱（XPS）进行了表征。FT-IR光谱表明，植物提取物中的生物活性分子含有多羟基，这些分子作为还原剂和配位剂，这一结论由TGA进一步证实。TEM和SEM显示，Fe3O4纳米颗粒呈近似球形，平均尺寸为50 nm。合成的Fe3O4纳米颗粒表现出铁磁性行为，饱和磁化强度为25.15 emu g−1。这些Fe3O4纳米颗粒在外部磁场下易于回收，对吡咯[3,4-c]喹啉-1,3-二酮衍生物表现出强烈的催化活性。这些结果表明，生产的Fe3O4纳米颗粒可作为有机合成中的催化剂，并且至少可以回收五次而不会显著损失其活性。

  DOI：

  10.1039/c4ra11623b

文献信息

• Efficient one-step synthesis of pyrrolo[3,4-c]quinoline-1,3-dione derivatives by organocatalytic cascade reactions of isatins and β-ketoamides
  作者：Likai Xia、Yong Rok Lee

  DOI：10.1039/c3ob40791h

  日期：——

  We describe an efficient one-step synthesis of pyrrolo[3,4-c]quinolinedione derivatives using ethylenediamine diacetate (EDDA)-catalyzed cascade reactions of isatins and β-ketoamides. It is the first direct conversion of isatins to pyrrolo[3,4-c]quinolinedione derivatives via C–N bond cleavage and isatin ring expansion. Furthermore, this reaction provides a one-step synthetic route for the production

  我们描述了一种高效的一步合成吡咯并[3,4- c ]喹啉二酮衍生物，使用乙二胺二乙酸酯（EDDA）催化的isatins和β-ketoamides级联反应。这是首次通过C–N键断裂和Isatin环扩环将Isatins直接转化为吡咯并[3,4- c ] quinolinedione衍生物。此外，该反应提供了一步合成路线，用于生产通常使用多步反应制备的生物学上感兴趣的复杂分子。
• Microwave-Assisted Synthesis of Diverse Pyrrolo[3,4-<i>c</i>]quinoline-1,3-diones and Their Antibacterial Activities
  作者：Likai Xia、Akber Idhayadhulla、Yong Rok Lee、Sung Hong Kim、Young-Jung Wee

  DOI：10.1021/co500002s

  日期：2014.7.14

  With the aim of developing a general and practical method for library production, a novel and efficient two-phase microwave-assisted cascade reaction between isatins and beta-ketoamides in [Bmim]BF4/toluene was developed for the synthesis of pyrrolo[3,4-c]quinoline-1,3-diones. The features of this methodology are, the use of microwave-assisted rapid synthesis, mild reaction conditions, high yields, operational simplicity, facile product separation, and recyclability. Furthermore, the antibacterial activities of the pyrrolo[3,4-c]quinoline-1,3-dione derivatives produced were evaluated against Gram-negative bacteria (Escherichia coli, Pseudomonas aeruginosa, and Enterobacter aerogenes) and Gram-positive bacteria (Bacillus cereus and Staphylococcus aureus). These derivatives showed antibacterial activities against Gram-positive strains that were at least equivalent to that against Gram-negative strains. Compound 73,5} displayed the most potent antibacterial activity against P. aeruginosa (MIC = 0.5 mu g/mL) and greater activity than standard ampicillin (MIC = 1 mu g/mL). Compound 74,7} exhibited the best inhibitory activity against E. coli and E. aerogenes (MIC = 1 and 0.5 mu g/mL), compared with the standard ampicillin (both MICs = 1 mu g/mL). The synthesized pyrrolo[3,4-c]quinoline-1,3-diones are expected to be widely used as lead compounds for the development of new antibacterial agents.
• [EN] QUINOLINE-CARBOXYLIC ACIDS AND THE DERIVATIVES THEREOF, A FOCUSED LIBRARY<br/>[FR] ACIDES QUINOLINE-CARBOXYLIQUES ET LEURS DERIVES ET BIBLIOTHEQUE FOCALISEE
  申请人：CHEMICAL DIVERSITY RES INST LT

  公开号：WO2004078731A1

  公开（公告）日：2004-09-16

  The invention relates to compounds, substituted guinoline-carboxylic acids and the derivatives thereof of general formula (1, 2, 3), the pharmaceutically acceptable salts thereof, N-oxides or hydrates and methods for the production thereof, a focused library, pharmaceutical compounds and the use thereof. Said compounds are embodied in the form of Caspase enzyme inhibitors and usefully used for curing various diseases associated to an increased apoptosis activity.