ethyl 2-oxo-1,2-dihydroquinoline-4-carboxylate

• 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: ethyl 2-oxo-1,2-dihydroquinoline-4-carboxylate
• 英文别名: ethyl 2-hydroxyquinoline-4-carboxylate
• 化学式: C₁₂H₁₁NO₃
• mdl: MFCD01925526
• 分子量: 217.224
• InChiKey: WTHATVQLTWYSCI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.166
• 拓扑面积：
  55.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  ethyl 2-oxo-1,2-dihydroquinoline-4-carboxylate 在 一水合肼 作用下， 以 乙醇 为溶剂， 以68%的产率得到2-oxo-1,2-dihydroquinoline-4-carbohydrazide
  参考文献：
  名称：

  Construction and functionalization of fused pyridine ring leading to novel compounds as potential antitubercular agents

  摘要：

  A series of fused and functionalized pyridine derivatives were designed, synthesized and tested for their potential antitubercular properties. All these novel compounds were prepared by using multistep methods involving the construction of pyridine ring as a key synthetic step. Some of these compounds were found to be interesting when tested for their antitubercular properties in vitro and one of them appeared as an attractive and potential antitubercular agent. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.05.096
• 作为产物：
  描述：

  alkaline earth salt of/the/ methylsulfuric acid 生成 ethyl 2-oxo-1,2-dihydroquinoline-4-carboxylate
  参考文献：
  名称：

  Koenigs; Koerner, Chemische Berichte, 1883, vol. 16, p. 2158

  摘要：

  DOI：

文献信息

• New alkyl (cyclohexyl) 2-oxo-1-(prop‑2-yn-1-yl)-1, 2-dihydroquinoline-4-carboxylates: Synthesis, crystal structure, spectroscopic characterization, hirshfeld surface analysis, molecular docking studies and DFT calculations
  作者：Sonia Hayani、Yusuf Sert、Yassir Filali Baba、Fouad Benhiba、Fouad Ouazzani Chahdi、Fatim-Zahra Laraqui、Joel T. Mague、Brahim El Ibrahimi、Nada Kheira Sebbar、Youssef Kandri Rodi、El Mokhtar Essassi

  DOI：10.1016/j.molstruc.2020.129520

  日期：2021.3

  Abstract An efficient synthesis of novel alkyl 2-oxo-1,2-dihydroquinoline-4-carboxylates (3a-3d) was developed, starting from 2-oxo-quinoline carboxylic acid 1a which successively undergoes esterification and alkylation reactions. The structures of all the obtained compounds were investigated and characterized by using 1H NMR and 13C NMR spectroscopic measurements. The molecular and crystal structures

  摘要 以 2-oxo-quinoline 羧酸 1a 为原料，通过酯化和烷基化反应，高效合成了新型 2-oxo-1,2-dihydroquinoline-4-carboxylates (3a-3d)。通过使用 1H NMR 和 13C NMR 光谱测量研究和表征所有获得的化合物的结构。四种化合物（3a、3b、3c 和 3d）的分子和晶体结构也已通过单晶 X 射线晶体学进行了检查。此外，还使用密度泛函理论 (DFT) 在 B3LYP/6-31G(d,p) 理论水平上获得了实验数据和预测光谱数据。此外，通过 Hirshfeld 表面分析、分子对接研究和 DFT 计算确定了四种结构的活性原子之间的最密切接触。实验结果与计算结果具有相关性，显示出很好的兼容性。最后，进行分子对接研究以研究标题化合物与蛋白质数据库（PDB：1M17-EGFR 激酶）抑制剂靶标的结合模式，并使用 Auto-Dock Vina
• Pd-Catalyzed Direct Cross-Coupling of Electron-Deficient Polyfluoroarenes with Heteroaromatic Tosylates
  作者：Shilu Fan、Jie Yang、Xingang Zhang

  DOI：10.1021/ol201706t

  日期：2011.8.19

  We report a Pd-catalyzed direct cross-coupling of electron-deficient polyfluoroarenes with heteroaromatic tosylates. The notable features of this reaction are its high reaction efficiency, excellent chemoselectivity, operational simplicity, and mild reaction conditions. We have applied this protocol to prepare the semiconducting materials in a highly efficient manner.

  我们报告了P​​d催化的电子不足的多氟芳烃与杂芳族甲苯磺酸盐的直接交叉偶联。该反应的显着特征是其高反应效率，优异的化学选择性，操作简便和温和的反应条件。我们已应用此协议以高效的方式制备半导体材料。
• Enantioselective, Intermolecular [_π2+_σ2] Photocycloaddition Reactions of 2(1<i>H</i>)-Quinolones and Bicyclo[1.1.0]butanes
  作者：Morgane de Robichon、Thilo Kratz、Frederike Beyer、Julian Zuber、Christian Merten、Thorsten Bach

  DOI：10.1021/jacs.3c08404

  日期：——

  enantioselectively to 2(1H)-quinolones upon irradiation (λ = 366 nm) in the presence of a chiral complexing agent. A two-point hydrogen bond between the quinolone and the template is responsible for stereocontrol in the photocycloaddition reaction. The reaction leads to the formation of products with a chiral bicyclo[2.1.1]hexane skeleton in high enantiomeric excess (91–99% ee). The chiral template can be almost

  在手性络合剂存在下，经照射 (λ = 366 nm)，1-取代的双环[1.1.0]丁烷对映选择性地加成到 2(1 H )-喹诺酮类药物上。喹诺酮和模板之间的两点氢键负责光​​环加成反应中的立体控制。该反应导致形成具有高对映体过量（91-99% ee）的手性双环[2.1.1]己烷骨架的产物。手性模板几乎可以定量（97%）回收并用于另一个反应。可能存在三重态反应途径，如果反应要在可见光 (λ = 420 nm) 下进行，则敏化是一个合适的工具。
• COMPOUNDS THAT ABROGATE THE CELL CYCLE G2 CHECKPOINT FOR USE IN THE TREATMENT OF CANCER
  申请人：CanBas Co., Ltd.

  公开号：EP3088397A1

  公开（公告）日：2016-11-02

  Substituted azole diones (II) and (III) are provided that kill cells, suppress cell proliferation, suppress cell growth, abrogate the cell cycle G2 checkpoint and/or cause adaptation to G2 cell cycle arrest. Methods of making the invention compounds are provided. The invention provides substituted azole diones (II) and (III) to treat cell proliferation disorders. The invention includes the substituted azole diones (II) and (III) for use to selectively kill or suppress cancer cells without additional anti-cancer treatment. The invention includes the cell cycle G2- checkpoint-abrogating substituted azole diones (II) and (III) for use to selectively sensitize cancer cells to DNA damaging reagents, treatments and/or other types of anti-cancer reagents.

  本发明提供的取代唑二酮类化合物(II)和(III)可杀死细胞、抑制细胞增殖、抑制细胞生长、减弱细胞周期 G2 检查点和/或导致适应 G2 细胞周期停滞。提供了制造本发明化合物的方法。本发明提供了用于治疗细胞增殖障碍的取代唑二酮类化合物（II）和（III）。本发明包括取代的唑二酮(II)和(III)，用于选择性地杀死或抑制癌细胞，而无需额外的抗癌治疗。本发明包括细胞周期G2-检查点消减取代的唑二酮(II)和(III)，用于选择性地使癌细胞对DNA损伤试剂、治疗和/或其它类型的抗癌试剂敏感。
• Design, Synthesis, and Biological Evaluation of Quinoline (Quinolinone) Derivatives as NADPH Oxidase (NOX) Inhibitors
  作者：Lei Zhang、Xinliang Yang、Rui Yi、Siming Wu、Qianbin Li、Gaoyun Hu、Zhuo Chen

  DOI：10.1111/cbdd.14610

  日期：2024.8

  oxygen species. Recent studies have shown that NOXs is a very promising target for the treatment of diabetic nephropathy (DN). Here, a series of quinoline(quinolinone) derivatives have been designed based on pharmacophore strategy, synthesized and evaluated. Among them, 19d exhibits potent antiproliferative and NOXs inhibitory activities, and is worthy for further investigation.

  NADPH氧化酶（NOX）是人体内唯一可以直接产生活性氧的酶。最近的研究表明，NOXs 是治疗糖尿病肾病（DN）的一个非常有前途的靶点。本文基于药效团策略设计、合成并评价了一系列喹啉（喹啉酮）衍生物。其中19d表现出有效的抗增殖和NOXs抑制活性，值得进一步研究。

表征谱图