4-methyl-2-(p-tolyl)-1H-pyrrolo[3,4-c]quinoline-1,3(2H)-dione | 687573-21-3

• 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: 4-methyl-2-(p-tolyl)-1H-pyrrolo[3,4-c]quinoline-1,3(2H)-dione
• 英文别名: 4-Methyl-2-(4-methylphenyl)-1H,2H,3H-pyrrolo[3,4-C]quinoline-1,3-dione；4-methyl-2-(4-methylphenyl)pyrrolo[3,4-c]quinoline-1,3-dione
• CAS: 687573-21-3
• 化学式: C₁₉H₁₄N₂O₂
• mdl: MFCD03829228
• 分子量: 302.332
• InChiKey: WUKYMQOEVYBXJH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  23
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  50.3
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-methyl-2-(p-tolyl)-1H-pyrrolo[3,4-c]quinoline-1,3(2H)-dione 、 对二甲氨基苯甲醛 在 哌啶 作用下， 以 邻二氯苯 为溶剂， 反应 4.0h， 以61%的产率得到4-(4-dimethylaminostyryl)-2-(p-tolyl)pyrrolo[3,4-c]quinoline-1,3-dione
  参考文献：
  名称：

  Synthesis and optical properties of copolymers of 4-aminostyrene with the side styrylquinoline chromophore groups

  摘要：

  连续的分子组装在聚合物链中形成了一系列含有侧链苯乙烯喹啉染料基团的梳形共聚物。研究了这些聚合物及低分子量模型染料的热学、热机械、光谱和发光特性。

  DOI：

  10.1007/s11172-011-0048-4
• 作为产物：
  描述：

  靛红 在 吡啶 、 乙酸酐 、 sodium hydroxide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 19.0h， 生成 4-methyl-2-(p-tolyl)-1H-pyrrolo[3,4-c]quinoline-1,3(2H)-dione
  参考文献：
  名称：

  Synthesis and optical properties of copolymers of 4-aminostyrene with the side styrylquinoline chromophore groups

  摘要：

  连续的分子组装在聚合物链中形成了一系列含有侧链苯乙烯喹啉染料基团的梳形共聚物。研究了这些聚合物及低分子量模型染料的热学、热机械、光谱和发光特性。

  DOI：

  10.1007/s11172-011-0048-4

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.
• Synthesis and optical properties of copolymers of 4-aminostyrene with the side styrylquinoline chromophore groups
  作者：M. Ya. Goikhman、L. I. Subbotina、A. A. Martynenkov、M. A. Smirnov、R. Yu. Smyslov、E. N. Popova、A. V. Yakimanskii

  DOI：10.1007/s11172-011-0048-4

  日期：2011.2

  Successive molecular assembling in polymer chains furnished a series of the comb-shaped copolymers of 4-aminostyrene containing side styrylquinoline chromophore groups. Thermal, thermomechanical, spectroscopic, and luminescent properties of the polymers and low-molecular-weight model chromophores were studied.

  连续的分子组装在聚合物链中形成了一系列含有侧链苯乙烯喹啉染料基团的梳形共聚物。研究了这些聚合物及低分子量模型染料的热学、热机械、光谱和发光特性。
• 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