(E)-1-(5-hydroxy-2,2-dimethyl-2H-chromen-8-yl)-3-(1-methyl-1H-indol-5-yl)prop-2-en-1-one | 1593929-30-6

• 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)-1-(5-hydroxy-2,2-dimethyl-2H-chromen-8-yl)-3-(1-methyl-1H-indol-5-yl)prop-2-en-1-one
• CAS: 1593929-30-6
• 化学式: C₂₃H₂₁NO₃
• 分子量: 359.425
• InChiKey: CLDPODXVPLWZLO-VMPITWQZSA-N

物化性质

• 沸点：
  604.6±55.0 °C(Predicted)
• 密度：
  1.18±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.96
• 重原子数：
  27.0
• 可旋转键数：
  3.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  51.46
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (E)-1-(5-hydroxy-2,2-dimethyl-2H-chromen-8-yl)-3-(1-methyl-1H-indol-5-yl)prop-2-en-1-one 、 异丁酸酐 在 吡啶 作用下， 反应 24.0h， 以63%的产率得到(E)-2,2-dimethyl-8-(3-(1-methyl-1H-indol-5-yl)acryloyl)-2H-chromen-5-yl isobutyrate
  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
• 作为产物：
  描述：

  2,4-二羟基苯乙酮 在 吡啶 、 copper(II) choride dihydrate 、 4-甲基苯磺酸吡啶 、 对甲苯磺酸 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 potassium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 水 、 乙腈 为溶剂， 反应 70.0h， 生成 (E)-1-(5-hydroxy-2,2-dimethyl-2H-chromen-8-yl)-3-(1-methyl-1H-indol-5-yl)prop-2-en-1-one
  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