2-(4-methoxybenzoyl)-3-(4-methoxyphenyl)quinoline | 1609013-26-4

• 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-methoxybenzoyl)-3-(4-methoxyphenyl)quinoline
• 英文别名: 3-(4-methoxylphenyl)-2-(4-methoxylbenzoyl)quinoline；(4-Methoxyphenyl)-[3-(4-methoxyphenyl)quinolin-2-yl]methanone；(4-methoxyphenyl)-[3-(4-methoxyphenyl)quinolin-2-yl]methanone
• CAS: 1609013-26-4
• 化学式: C₂₄H₁₉NO₃
• 分子量: 369.42
• InChiKey: SPSOPTGYXPMDKI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  28
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  48.4
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-(4-methoxybenzoyl)-3-(4-methoxyphenyl)quinoline 在 氢溴酸 作用下， 反应 48.0h， 以90%的产率得到2-(4-hydroxybenzoyl)-3-(4-hydroxyphenyl)quinoline
  参考文献：
  名称：

  Synthesis, antiproliferative and anti-dengue virus evaluations of 2-aroyl-3-arylquinoline derivatives

  摘要：

  A number of 2-aroy1-3-arylquinoline derivatives was synthesized and evaluated for their anti-Dengue virus activity. Both 2-(hydroxyphenylmethyl)-3-(4-methoxyphenyl)quinoline (13a) and 2-(4-hydroxybenzoyl)-3-(4-hydroxyphenyl)quinoline (17) were found to significantly inhibit the DENV2 RNA expression in Huh-7-DV-Fluc cells with a potency approximately equal to that of ribavirin and the inhibition is in a dose-dependent manner. Compounds 13a and 17 reduced DENV replication in both viral protein and mRNA levels, and no significant cell cytotoxicity was detected, with greater than 50% viability of Huh-7-DV-Fluc cells at a concentration of 100 mu M. However, significant cytotoxicity was detected for the positive ribavirin. In addition, we performed infectious assay to further verify the inhibitory activity of 13a and 17 on DENV replication in protein and RNA levels. On the other hand, compounds 19a-19c exhibited IC50 values ranged from 4.47 to 8.68 1iM against A549, H1299, MCF-7, and Huh-7 which were approximately equal potent to the positive topotecan. Structural optimization of lead compounds, 13a and 17, and their detailed molecular mechanism of action are ongoing. (C) 2014 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2014.03.074
• 作为产物：
  描述：

  3-(4-methoxyphenyl)quinolin-2-carbaldehyde 在 manganese(IV) oxide 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 24.0h， 生成 2-(4-methoxybenzoyl)-3-(4-methoxyphenyl)quinoline
  参考文献：
  名称：

  Synthesis, antiproliferative and anti-dengue virus evaluations of 2-aroyl-3-arylquinoline derivatives

  摘要：

  A number of 2-aroy1-3-arylquinoline derivatives was synthesized and evaluated for their anti-Dengue virus activity. Both 2-(hydroxyphenylmethyl)-3-(4-methoxyphenyl)quinoline (13a) and 2-(4-hydroxybenzoyl)-3-(4-hydroxyphenyl)quinoline (17) were found to significantly inhibit the DENV2 RNA expression in Huh-7-DV-Fluc cells with a potency approximately equal to that of ribavirin and the inhibition is in a dose-dependent manner. Compounds 13a and 17 reduced DENV replication in both viral protein and mRNA levels, and no significant cell cytotoxicity was detected, with greater than 50% viability of Huh-7-DV-Fluc cells at a concentration of 100 mu M. However, significant cytotoxicity was detected for the positive ribavirin. In addition, we performed infectious assay to further verify the inhibitory activity of 13a and 17 on DENV replication in protein and RNA levels. On the other hand, compounds 19a-19c exhibited IC50 values ranged from 4.47 to 8.68 1iM against A549, H1299, MCF-7, and Huh-7 which were approximately equal potent to the positive topotecan. Structural optimization of lead compounds, 13a and 17, and their detailed molecular mechanism of action are ongoing. (C) 2014 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2014.03.074

文献信息

• Copper-Catalyzed Aerobic Oxidation and Oxygenation of Anilines and Acetaldehydes with Dioxygen for the Concise Synthesis of 2-Aroylquinolines
  作者：Ziyuan Li、Ning Jiao、Xiaoyang Wang、Lifang Ma

  DOI：10.1055/s-0036-1588171

  日期：2017.8

  A concise and efficient aerobic oxidation and oxygenation approach for the construction of 2-aroylquinolines has been developed through copper-catalyzed annulation of anilines, acetaldehydes, and dioxygen. 2,2,6,6-Tetramethylpiperidine-1-oxyl was employed to direct the selectivity toward the desired 2-aroyl products. Molecular oxygen was used in this transformation as an environmentally benign source

  通过铜催化苯胺、乙醛和双氧的环化，开发了一种简洁有效的有氧氧化和氧化方法，用于构建 2-芳酰基喹啉。2,2,6,6-四甲基哌啶-1-氧基用于将选择性导向所需的2-芳酰基产物。在这种转化中，分子氧被用作环境友好的氧源。
• Synthesis, antiproliferative and anti-dengue virus evaluations of 2-aroyl-3-arylquinoline derivatives
  作者：Chih-Hua Tseng、Chun-Kuang Lin、Yeh-Long Chen、Chih-Yao Hsu、Huey-Nan Wu、Chin-Kai Tseng、Jin-Ching Lee

  DOI：10.1016/j.ejmech.2014.03.074

  日期：2014.5

  A number of 2-aroy1-3-arylquinoline derivatives was synthesized and evaluated for their anti-Dengue virus activity. Both 2-(hydroxyphenylmethyl)-3-(4-methoxyphenyl)quinoline (13a) and 2-(4-hydroxybenzoyl)-3-(4-hydroxyphenyl)quinoline (17) were found to significantly inhibit the DENV2 RNA expression in Huh-7-DV-Fluc cells with a potency approximately equal to that of ribavirin and the inhibition is in a dose-dependent manner. Compounds 13a and 17 reduced DENV replication in both viral protein and mRNA levels, and no significant cell cytotoxicity was detected, with greater than 50% viability of Huh-7-DV-Fluc cells at a concentration of 100 mu M. However, significant cytotoxicity was detected for the positive ribavirin. In addition, we performed infectious assay to further verify the inhibitory activity of 13a and 17 on DENV replication in protein and RNA levels. On the other hand, compounds 19a-19c exhibited IC50 values ranged from 4.47 to 8.68 1iM against A549, H1299, MCF-7, and Huh-7 which were approximately equal potent to the positive topotecan. Structural optimization of lead compounds, 13a and 17, and their detailed molecular mechanism of action are ongoing. (C) 2014 Elsevier Masson SAS. All rights reserved.