(E)-3-(3-(4-methoxyphenyl)quinolin-2-yl)-1-phenylprop-2-en-1-one | 1422526-45-1

• 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: (E)-3-(3-(4-methoxyphenyl)quinolin-2-yl)-1-phenylprop-2-en-1-one
• 英文别名: (E)-3-[3-(4-methoxyphenyl)quinolin-2-yl]-1-phenylprop-2-en-1-one
• CAS: 1422526-45-1
• 化学式: C₂₅H₁₉NO₂
• 分子量: 365.431
• InChiKey: VTEKZHZSRZBDPE-FOCLMDBBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  28
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.04
• 拓扑面积：
  39.2
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  3-(4-methoxyphenyl)-2-methylquinoline 在 selenium(IV) oxide 、 potassium hydroxide 作用下， 以 1,4-二氧六环 、 水 为溶剂， 反应 2.0h， 生成 (E)-3-(3-(4-methoxyphenyl)quinolin-2-yl)-1-phenylprop-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 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.
• Synthesis and antiproliferative evaluation of 3-phenylquinolinylchalcone derivatives against non-small cell lung cancers and breast cancers
  作者：Chih-Hua Tseng、Yeh-Long Chen、Chih-Yao Hsu、Tzu-Chiang Chen、Chih-Mei Cheng、Hsien-Cheng Tso、Yan-Jia Lu、Cherng-Chyi Tzeng

  DOI：10.1016/j.ejmech.2012.11.027

  日期：2013.1

  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.