6-fluoro-3-(4-methoxyphenyl)-2-methylquinoline-4-carboxylic acid | 1609013-04-8

• 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: 6-fluoro-3-(4-methoxyphenyl)-2-methylquinoline-4-carboxylic acid
• CAS: 1609013-04-8
• 化学式: C₁₈H₁₄FNO₃
• 分子量: 311.312
• InChiKey: AUCGDQWUPGMXPV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.06
• 重原子数：
  23.0
• 可旋转键数：
  3.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  59.42
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  6-fluoro-3-(4-methoxyphenyl)-2-methylquinoline-4-carboxylic acid 在 selenium(IV) oxide 、 邻二氯苯 作用下， 以 1,4-二氧六环 为溶剂， 反应 6.0h， 生成 6-fluoro-3-(4-methoxyphenyl)quinoline-2-carbaldehyde
  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：

  5-氟靛红 、 对甲氧基苯基丙酮 在 potassium hydroxide 作用下， 以 乙醇 为溶剂， 反应 48.0h， 以93%的产率得到6-fluoro-3-(4-methoxyphenyl)-2-methylquinoline-4-carboxylic acid
  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

• Discovery of 2-[2-(5-nitrofuran-2-yl)vinyl]quinoline derivatives as a novel type of antimetastatic agents
  作者：Chih-Hua Tseng、Cherng-Chyi Tzeng、Chien-Chih Chiu、Chih-Yao Hsu、Chon-Kit Chou、Yeh-Long Chen

  DOI：10.1016/j.bmc.2014.11.015

  日期：2015.1

  2-furanylvinylquinoline derivatives were synthesized and evaluated for antiproliferative activities against the growth of four cancer cell lines including non-small cell lung cancer (A549 and H1299), breast cancer (MCF-7 and MDA-MB-231) and normal diploid embryonic lung cell line (MRC-5). Among them, (E)-6-methoxy-3-(4-methoxyphenyl)-2-[2-(5-nitrofuran-2-yl)vinyl]quinoline (10c) was found low cytotoxic

  合成了多种2-呋喃基乙烯基喹啉衍生物，并评估了其对四种癌细胞系（包括非小细胞肺癌（A549和H1299），乳腺癌（MCF-7和MDA-MB-231）和正常细胞）的生长的抗增殖活性。二倍体胚胎肺细胞系（MRC-5）。其中，在所有癌细胞和正常细胞中发现（E）-6-甲氧基-3-（4-甲氧基苯基）-2- [2-（5-硝基呋喃-2-基）乙烯基]喹啉（10c）具有低细胞毒性。 。这项研究的目的是研究化合物10c在H1299人肺癌细胞中的抗侵袭和抗转移活性。在这项研究中，化合物10c通过伤口愈合试验和transwell入侵试验以浓度依赖的方式抑制细胞的迁移和侵袭。此外，化合物10c对Akt和ERK磷酸化的抑制可能对细胞迁移至关重要，这可能导致与细胞迁移相关的多种因素的下调，包括β-catenin转录因子，Bcl-2和COX- 2。有趣的是，化合物10c的处理不影响表达水平，但降低了MMP-2和-9的活性
• Discovery of 3-phenylquinolinylchalcone derivatives as potent and selective anticancer agents against breast cancers
  作者：Chih-Hua Tseng、Cherng-Chyi Tzeng、Chih-Yao Hsu、Chih-Mei Cheng、Chia-Ning Yang、Yeh-Long Chen

  DOI：10.1016/j.ejmech.2015.04.054

  日期：2015.6

  A number of 3-phenylquinolinylchalcone derivatives were synthesized and evaluated in vitro for their antiproliferative activities against three breast cancer cell lines (MCF-7, MDA-MB-231, and SKBR-3), and a non-cancer normal epithelial cell line (H184B5F5/M10). Among them, (E)-3-[3-(4-methoxyphenyl)quinolin-2-yl]-1-(3,4,5-trimethoxyphenyl)prop-2-en-1-one (7) was active against the growth of MCF-7, MDA-MB-231, and SKBR-3 with IC50 values of 1.05, 0.75, and 0.78 mu M respectively without significant cytotoxicity to the normal H184B5F5/M10 cell line and therefore, was selected as a new lead for further mechanism studies. Results indicated that compound 7 inhibited the polymerization of tubulins, induced G2/M cell cycle arrest via modulation of the cyclin B1, cdk1 and CDC25. Compound 7 ultimately induced cell apoptosis by the increase of apoptotic protein Bax and the decrease of anti-apoptotic protein Bcl-2. In addition, PARP was cleaved while caspase-3 and -8 activities were induced after the treatment of compound 7 for 24 h in a concentration-dependent manner. Thus, compound 7 induces cell cycle arrest at G2/M phase via cleavage of PARP, induces caspase-3 and -8 activities and consequently to cause the cell death. Further study on the structure optimization of 7 is ongoing. (C) 2015 Elsevier Masson SAS. All rights reserved.