6-chloro-3-((1E,4Z,6E)-5-hydroxy-7-(4-hydroxy-3-methoxyphenyl)-3-oxohepta-1,4,6-trienyl)-6-methyl-1-(prop-2-ynyl)quinolin-2(1H)-one

• 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-chloro-3-((1E,4Z,6E)-5-hydroxy-7-(4-hydroxy-3-methoxyphenyl)-3-oxohepta-1,4,6-trienyl)-6-methyl-1-(prop-2-ynyl)quinolin-2(1H)-one
• 英文别名: 6-chloro-3-[(1E,4Z,6E)-5-hydroxy-7-(4-hydroxy-3-methoxyphenyl)-3-oxohepta-1,4,6-trienyl]-1-prop-2-ynylquinolin-2-one
• 化学式: C₂₆H₂₀ClNO₅
• 分子量: 461.901
• InChiKey: OFNQUHRXJBYUHE-HOIRTMKVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  33
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  87.1
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  2,6-二氯喹啉-3-甲醛 在 盐酸 、 水 、 potassium carbonate 、 正丁胺 作用下， 以 甲醇 、 水 、 乙酸乙酯 、 N,N-二甲基甲酰胺 为溶剂， 生成 6-chloro-3-((1E,4Z,6E)-5-hydroxy-7-(4-hydroxy-3-methoxyphenyl)-3-oxohepta-1,4,6-trienyl)-6-methyl-1-(prop-2-ynyl)quinolin-2(1H)-one
  参考文献：
  名称：

  Synthesis and anticancer activity of novel curcumin–quinolone hybrids

  摘要：

  A number of new curcumin-quinolone hybrids were synthesised from differently substituted 3-formyl-2-quinolones and vanillin and their in vitro cytotoxicity was determined on a panel of representative cell lines (A549, MCF7, SKOV3 and H460) using MTT assay. The most potent compound 14, was analysed for its mode of action using various cell biology experiments. SKOV3 cells treated with compound 14 showed distorted cell morphology under phase contrast imaging and induction of apoptosis was confirmed by Annexin V/PE assay. Further experiments on generation of reactive oxygen species (ROS) and cell cycle analysis revealed that these hybrids induce apoptosis by ROS generation and arrest cell cycle progression in S and G2/M phase. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2015.06.068

文献信息

• Synthesis and anticancer activity of novel curcumin–quinolone hybrids
  作者：Saiharish Raghavan、Prasath Manogaran、Krishna Kumari Gadepalli Narasimha、Balasubramanian Kalpattu Kuppusami、Palanivelu Mariyappan、Anjana Gopalakrishnan、Ganesh Venkatraman

  DOI：10.1016/j.bmcl.2015.06.068

  日期：2015.9

  A number of new curcumin-quinolone hybrids were synthesised from differently substituted 3-formyl-2-quinolones and vanillin and their in vitro cytotoxicity was determined on a panel of representative cell lines (A549, MCF7, SKOV3 and H460) using MTT assay. The most potent compound 14, was analysed for its mode of action using various cell biology experiments. SKOV3 cells treated with compound 14 showed distorted cell morphology under phase contrast imaging and induction of apoptosis was confirmed by Annexin V/PE assay. Further experiments on generation of reactive oxygen species (ROS) and cell cycle analysis revealed that these hybrids induce apoptosis by ROS generation and arrest cell cycle progression in S and G2/M phase. (C) 2015 Elsevier Ltd. All rights reserved.