(E)-2,2-dimethyl-8-(3-(1-methyl-1H-indol-5-yl)acryloyl)-2H-chromen-5-yl acetate | 1593929-33-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: (E)-2,2-dimethyl-8-(3-(1-methyl-1H-indol-5-yl)acryloyl)-2H-chromen-5-yl acetate
• 英文别名: [2,2-dimethyl-8-[(E)-3-(1-methylindol-5-yl)prop-2-enoyl]chromen-5-yl] acetate
• CAS: 1593929-33-9
• 化学式: C₂₅H₂₃NO₄
• 分子量: 401.462
• InChiKey: SVOVJCRYNGJTAK-RMKNXTFCSA-N

物化性质

• 沸点：
  614.4±55.0 °C(predicted)
• 密度：
  1.17±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  30
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  57.5
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  1-甲基-1H-吲哚-5-甲醛 在 吡啶 、 对甲苯磺酸 、 potassium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 水 为溶剂， 反应 73.0h， 生成 (E)-2,2-dimethyl-8-(3-(1-methyl-1H-indol-5-yl)acryloyl)-2H-chromen-5-yl acetate
  参考文献：
  名称：

  Design, synthesis and biological evaluation of a series of pyrano chalcone derivatives containing indole moiety as novel anti-tubulin agents

  摘要：

  A new series of pyrano chalcone derivatives containing indole moiety (3-42, 49a-49r) were synthesized and evaluated for their antiproliferative activities. Among all the compounds, compound 49b with a propionyloxy group at the 4-position of the left phenyl ring and N-methyl-5-indoly on the right ring displayed the most potent cytotoxic activity against all tested cancer cell lines including multidrug resistant phenotype, which inhibits cancer cell growth with IC50 values ranging from 0.22 to 1.80 mu M. Furthermore, 49b significantly induced cell cycle arrest in G2/M phase and inhibited the polymerization of tubulin. Molecular docking analysis demonstrated the interaction of 49b at the colchicine binding site of tubulin. In experiments in vivo, 49b exerted potent anticancer activity in HepG2 human liver carcinoma in BALB/c nude mice. These results indicated these compounds are promising inhibitors of tubulin polymerization for the potential treatment of cancer. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2014.02.028

文献信息

• Design, synthesis and biological evaluation of a series of pyrano chalcone derivatives containing indole moiety as novel anti-tubulin agents
  作者：Guangcheng Wang、Chunyan Li、Lin He、Kai Lei、Fang Wang、Yuzi Pu、Zhuang Yang、Dong Cao、Liang Ma、Jinying Chen、Yun Sang、Xiaolin Liang、Mingli Xiang、Aihua Peng、Yuquan Wei、Lijuan Chen

  DOI：10.1016/j.bmc.2014.02.028

  日期：2014.4

  A new series of pyrano chalcone derivatives containing indole moiety (3-42, 49a-49r) were synthesized and evaluated for their antiproliferative activities. Among all the compounds, compound 49b with a propionyloxy group at the 4-position of the left phenyl ring and N-methyl-5-indoly on the right ring displayed the most potent cytotoxic activity against all tested cancer cell lines including multidrug resistant phenotype, which inhibits cancer cell growth with IC50 values ranging from 0.22 to 1.80 mu M. Furthermore, 49b significantly induced cell cycle arrest in G2/M phase and inhibited the polymerization of tubulin. Molecular docking analysis demonstrated the interaction of 49b at the colchicine binding site of tubulin. In experiments in vivo, 49b exerted potent anticancer activity in HepG2 human liver carcinoma in BALB/c nude mice. These results indicated these compounds are promising inhibitors of tubulin polymerization for the potential treatment of cancer. (C) 2014 Elsevier Ltd. All rights reserved.