2-(hydroxy-3,4,5-trimethoxyphenylmethyl)-3-(4-methoxyphenyl)quinoline | 1609013-25-3

• 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: 2-(hydroxy-3,4,5-trimethoxyphenylmethyl)-3-(4-methoxyphenyl)quinoline
• 英文别名: [3-(4-Methoxyphenyl)quinolin-2-yl]-(3,4,5-trimethoxyphenyl)methanol；[3-(4-methoxyphenyl)quinolin-2-yl]-(3,4,5-trimethoxyphenyl)methanol
• CAS: 1609013-25-3
• 化学式: C₂₆H₂₅NO₅
• 分子量: 431.488
• InChiKey: MKFUMDULKWXQQA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  32
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  70
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2-(hydroxy-3,4,5-trimethoxyphenylmethyl)-3-(4-methoxyphenyl)quinoline 在 manganese(IV) oxide 作用下， 以 二氯甲烷 为溶剂， 反应 12.0h， 以82%的产率得到2-(3,4,5-trimethoxybenzoyl)-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
• 作为产物：
  描述：

  3-(4-methoxyphenyl)quinolin-2-carbaldehyde 、 magnesium,1,2,3-trimethoxybenzene-5-ide,bromide 以 四氢呋喃 为溶剂， 反应 12.0h， 以54%的产率得到2-(hydroxy-3,4,5-trimethoxyphenylmethyl)-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

• 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.