2-(4-chlorophenyl)-4-methyl-1H-pyrrolo[3,4-c]quinoline-1,3(2H)-dione | 1448778-49-1

• 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-chlorophenyl)-4-methyl-1H-pyrrolo[3,4-c]quinoline-1,3(2H)-dione
• 英文别名: 2-(4-Chlorophenyl)-4-methylpyrrolo[3,4-c]quinoline-1,3-dione；2-(4-chlorophenyl)-4-methylpyrrolo[3,4-c]quinoline-1,3-dione
• CAS: 1448778-49-1
• 化学式: C₁₈H₁₁ClN₂O₂
• 分子量: 322.751
• InChiKey: QYRMDFLOVPHLAT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  23
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  50.3
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  靛红 在 对甲苯磺酸一水合物 、 potassium hydroxide 作用下， 以 1,4-二氧六环 、 水 为溶剂， 反应 15.5h， 生成 2-(4-chlorophenyl)-4-methyl-1H-pyrrolo[3,4-c]quinoline-1,3(2H)-dione
  参考文献：
  名称：

  发现一类新的有效吡咯并[3,4-c]喹啉-1,3-二酮类人二氢乳清酸脱氢酶抑制剂：合成、药理学和毒理学评价

  摘要：

  通过 Pfitzinger 喹啉酯前体与选定的芳香胺、杂芳香胺和脂肪胺的环化反应合成了二十个取代的吡咯并[3,4-]喹啉-1,3-二酮。所有衍生物的结构均通过IR、H NMR、C NMR 和HRMS 光谱进行确认，同时使用HPLC 技术测定其纯度。几乎所有化合物都被鉴定为一类新的hDHODH强效抑制剂，其中 和 是活性最强的化合物，其IC50值相同，为0.11 μM，比参考药物来氟米特好约7倍。这两种衍生物还对健康 HaCaT 细胞表现出非常低的细胞毒性作用，并在生理 pH 值下通过实验获得了最佳亲脂特性，logP 值分别为 1.12 和 2.07。我们进一步评估了三种最活跃的化合物和参考药物来氟米特的毒理学影响的比较差异。将大鼠分为5组，腹腔注射治疗，对照组（I组）单剂量来氟米特（20 mg/kg），II组，其余三组（III、IV、V）腹腔注射，（20毫克/千克体重）单独。通过检查血清生

  DOI：

  10.1016/j.bioorg.2024.107359

文献信息

• Sonochemically synthesized ferromagnetic Fe₃O₄nanoparticles as a recyclable catalyst for the preparation of pyrrolo[3,4-c]quinoline-1,3-dione derivatives
  作者：Nagaraj Basavegowda、Kanchan Mishra、Yong Rok Lee

  DOI：10.1039/c4ra11623b

  日期：——

  This paper reports the green, rapid synthesis of Fe3O4 nanoparticles by the ultrasonic irradiation of Fe2O3 solution and Perilla frutescens (P. frutescens) leaf extract, which was used as both reducing and capping agent. The synthesized Fe3O4 nanoparticles were characterized by Fourier transform infrared spectroscopy (FT-IR), X-ray diffraction (XRD), transmission electron microscopy (TEM), scanning electron microscopy (SEM), energy dispersive X-ray analysis, vibrating sample magnetometry, thermogravimetric analysis (TGA) and X-ray photoelectron spectroscopy (XPS). The FT-IR spectra indicated that the bioactive molecules present in the plant extract contain polyols, which act as a reducing as well as capping agent, as confirmed by TGA. TEM and SEM showed that the Fe3O4 nanoparticles were approximately spherical in shape with a mean size of 50 nm. The synthesized Fe3O4 nanoparticles exhibited ferromagnetic behavior with a saturation magnetization of 25.15 emu g−1. The Fe3O4 nanoparticles, with their easy recovery by an external magnetic field, exhibited strong catalytic activity towards pyrrolo[3,4-c]quinoline-1,3-dione derivatives. These results suggest that the Fe3O4 nanoparticles produced can be applied as a catalyst in organic synthesis and recycled at least five times without significant loss in its activity.

  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。
• 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.
• Discovery of a new class of potent pyrrolo[3,4-c]quinoline-1,3-diones based inhibitors of human dihydroorotate dehydrogenase: Synthesis, pharmacological and toxicological evaluation
  作者：Marina G. Dimitrijević、Cornelia Roschger、Kevin Lang、Andreas Zierer、Milica G. Paunović、Ana D. Obradović、Miloš M. Matić、Marijana Pocrnić、Nives Galić、Andrija Ćirić、Milan D. Joksović

  DOI：10.1016/j.bioorg.2024.107359

  日期：2024.6

  Twenty -substituted pyrrolo[3,4-]quinoline-1,3-diones were synthesized by a cyclization reaction of Pfitzinger's quinoline ester precursor with the selected aromatic, heteroaromatic and aliphatic amines. The structures of all derivatives were confirmed by IR, H NMR, C NMR and HRMS spectra, while their purity was determined using HPLC techniques. Almost all compounds were identified as a new class ofpotent

  通过 Pfitzinger 喹啉酯前体与选定的芳香胺、杂芳香胺和脂肪胺的环化反应合成了二十个取代的吡咯并[3,4-]喹啉-1,3-二酮。所有衍生物的结构均通过IR、H NMR、C NMR 和HRMS 光谱进行确认，同时使用HPLC 技术测定其纯度。几乎所有化合物都被鉴定为一类新的hDHODH强效抑制剂，其中 和 是活性最强的化合物，其IC50值相同，为0.11 μM，比参考药物来氟米特好约7倍。这两种衍生物还对健康 HaCaT 细胞表现出非常低的细胞毒性作用，并在生理 pH 值下通过实验获得了最佳亲脂特性，logP 值分别为 1.12 和 2.07。我们进一步评估了三种最活跃的化合物和参考药物来氟米特的毒理学影响的比较差异。将大鼠分为5组，腹腔注射治疗，对照组（I组）单剂量来氟米特（20 mg/kg），II组，其余三组（III、IV、V）腹腔注射，（20毫克/千克体重）单独。通过检查血清生