(E)-1-(2,4-dimethoxyphenyl)-3-[3-(4-methoxyphenyl)quinolin-2-yl]prop-2-en-1-one | 1422526-49-5

• 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: (E)-1-(2,4-dimethoxyphenyl)-3-[3-(4-methoxyphenyl)quinolin-2-yl]prop-2-en-1-one
• CAS: 1422526-49-5
• 化学式: C₂₇H₂₃NO₄
• 分子量: 425.484
• InChiKey: YUZKSNNRXKBGSR-CCEZHUSRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  32
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  57.6
• 氢给体数：
  0
• 氢受体数：
  5

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)-1-(2,4-dimethoxyphenyl)-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

• 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.