3-(4-fluorophenyl)-2-methylquinoline | 1260519-60-5

• 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: 3-(4-fluorophenyl)-2-methylquinoline
• CAS: 1260519-60-5
• 化学式: C₁₆H₁₂FN
• 分子量: 237.276
• InChiKey: OUWRIUHWVVLRAU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.35
• 重原子数：
  18.0
• 可旋转键数：
  1.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  12.89
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  3-(4-fluorophenyl)-2-methylquinoline 在 manganese(IV) oxide 、 selenium(IV) oxide 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 二氯甲烷 为溶剂， 反应 26.0h， 生成 2-benzoyl-3-(4-fluorophenyl)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-fluorophenyl)-2-methylquinoline-4-carboxylic acid 在 邻二氯苯 作用下， 反应 4.0h， 以75%的产率得到3-(4-fluorophenyl)-2-methylquinoline
  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

• Carbon Atom Insertion into Pyrroles and Indoles Promoted by Chlorodiazirines
  作者：Balu D. Dherange、Patrick Q. Kelly、Jordan P. Liles、Matthew S. Sigman、Mark D. Levin

  DOI：10.1021/jacs.1c06287

  日期：2021.8.4

  calculations supporting a selectivity-determining cyclopropanation step. Computations surprisingly indicate that the stereochemistry of cyclopropanation is of little consequence to the subsequent electrocyclic ring opening that forges the pyridine core, due to a compensatory homoaromatic stabilization that counterbalances orbital-controlled torquoselectivity effects. The utility of this skeletal transform is

  在这里，我们报告了一种反应，该反应通过将芳基羰基阳离子等价物分别插入吡咯和吲哚核心选择性地产生 3-芳基吡啶和喹啉基序。通过使用 α-chlorodiazirines 作为相应氯卡宾的热前体，可以修改作为母体 Ciamician-Denstedt 重排核心的传统基于卤仿的协议，以直接提供 3-（杂）芳基吡啶和喹啉。通过氧化可商购的脒鎓盐可方便地在一个步骤中制备氯二氮嗪。检测了作为吡咯取代模式函数的选择性，并提出了基于空间效应的预测模型，DFT 计算支持确定选择性的环丙烷化步骤。计算出人意料地表明，环丙烷化的立体化学对随后形成吡啶核心的电环开环几乎没有影响，这是由于补偿性同芳族稳定化抵消了轨道控制的扭矩选择性效应。通过喹啉的制备和药学相关吡咯的骨架编辑进一步证明了这种骨架转化的效用。
• Heteroatom-Guided, Palladium-Catalyzed Regioselective C–H Functionalization in the Synthesis of 3-Arylquinolines
  作者：Virendra Kumar Tiwari、Govind Goroba Pawar、Riki Das、Amit Adhikary、Manmohan Kapur

  DOI：10.1021/ol401349a

  日期：2013.7.5

  A new approach for the regioselective functionalization of the C-3-position of quinolines is described. The method utilizes heteroatom guided regioselective C-3 palladation followed by arylation via transmetalation with aryl boronic acids to yield 3-aryl-N-acyl-1,2-dihydroquinolines. In a one-pot sequence, N-deacylation followed by aromatization leads to important 3-arylquinolines in good yields.