3-(4-methoxyphenyl)-2-methylquinoline-4-carboxylic acid | 24260-29-5

• 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-methoxyphenyl)-2-methylquinoline-4-carboxylic acid
• CAS: 24260-29-5
• 化学式: C₁₈H₁₅NO₃
• 分子量: 293.322
• InChiKey: DQJNMVYGZQXAJW-UHFFFAOYSA-N

物化性质

• 沸点：
  422.0±45.0 °C(Predicted)
• 密度：
  1.248±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.92
• 重原子数：
  22.0
• 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：

  3-(4-methoxyphenyl)-2-methylquinoline-4-carboxylic acid 在 selenium(IV) oxide 、 potassium hydroxide 作用下， 以 1,4-二氧六环 、 水 为溶剂， 反应 6.0h， 生成 (E)-1-(3-aminothiophen-2-yl)-3-[3-(4-methoxyphenyl)quinolin-2-yl]prop-2-en-1-one
  参考文献：
  名称：

  Synthesis and antiproliferative evaluation of 3-phenylquinolinylchalcone derivatives against non-small cell lung cancers and breast cancers

  摘要：

  Certain 3-phenylquinolinylchalcone derivatives were synthesized and evaluated for their antiproliferative activities. Among them, (E)-3-(3-(4-methoxyphenyl)quinolin-2-yl)-1-phenylprop-2-en-1-one (6a) and (E)-1-(5-bromothiophen-2-yl)-3-(3-(4-methoxyphenyl)quinolin-2-yeprop-2-en-1-one (11) were identified as potential lead compounds for further development. Compound 6a was active against the growth of H1299 and SKBR-3 with IC50 values of 1.41 and 0.70 mu M respectively which was more active than the positive topotecan (IC50 values of 6.02 and 8.91 mu M respectively). Compound 11 exhibited an IC50 value of less than 0.10 mu M against the growth of MDA-MB231, and non-cytotoxic to the normal mammary epithelial cell (H184B5F5/M10). Mechanism studies indicated that compound 11 induced cell cycle arrest at G2/M phase followed by activation of caspase-3, cleavage of PARP, and consequently caused the cell death. (C) 2012 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2012.11.027

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