(E)-N'-[3-(4-hydroxy-3,5-dimethoxyphenyl)acryloyl]-4-methoxybenzohydrazide

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: (E)-N'-[3-(4-hydroxy-3,5-dimethoxyphenyl)acryloyl]-4-methoxybenzohydrazide
• 英文别名: N'-[(E)-3-(4-hydroxy-3,5-dimethoxyphenyl)prop-2-enoyl]-4-methoxybenzohydrazide
• 化学式: C₁₉H₂₀N₂O₆
• 分子量: 372.378
• InChiKey: XUQWPKARACNQBY-RUDMXATFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  27
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.16
• 拓扑面积：
  106
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  丁香醛 在 哌啶 、 (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate 、 三乙胺 作用下， 以 吡啶 、 N,N-二甲基甲酰胺 为溶剂， 生成 (E)-N'-[3-(4-hydroxy-3,5-dimethoxyphenyl)acryloyl]-4-methoxybenzohydrazide
  参考文献：
  名称：

  Synthesis and biological evaluation of hydroxycinnamic acid hydrazide derivatives as inducer of caspase-3

  摘要：

  In order to generate compounds with superior antitumor activity and reduced toxicity, twelve new hydroxycinnamic acid hydrazide derivatives were synthesized and evaluated for their antiproliferative activities against two cancer cell lines (H1299 lung carcinoma cells and MCF-7 breast cancer cells), and compared to two normal counterparts (NL-20 lung epithelial cells and H184B5F5/M10 breast cells) by MIT method. The results demonstrated that some of these compounds possessed good antiproliferative activity against the two cancer cell lines. Among them, compound 2c was active against the growth of H1299 lung carcinoma cells with IC50 values of 1.50 mu M, which was more active than the positive topotecan (IC50 = 4.18 mu M). Simultaneously, it showed lower cytotoxic effects on normal NL-20 lung epithelial cells (IC50 > 10 mu M). Mechanism studies indicated that it induced cell cycle arrest at G2/M phase followed by activation of caspase-3, and consequently caused the cell death. Further studies on the structure optimization are ongoing. (C) 2014 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2014.08.040

文献信息

• Synthesis and biological evaluation of hydroxycinnamic acid hydrazide derivatives as inducer of caspase-3
  作者：Zheng-Rong Wu、Jian Liu、Jian-Ying Li、Li-Fang Zheng、Yang Li、Xing Wang、Qing-Jian Xie、Ai-Xia Wang、Ying-Hui Li、Rong-Hui Liu、Hong-Yu Li

  DOI：10.1016/j.ejmech.2014.08.040

  日期：2014.10

  In order to generate compounds with superior antitumor activity and reduced toxicity, twelve new hydroxycinnamic acid hydrazide derivatives were synthesized and evaluated for their antiproliferative activities against two cancer cell lines (H1299 lung carcinoma cells and MCF-7 breast cancer cells), and compared to two normal counterparts (NL-20 lung epithelial cells and H184B5F5/M10 breast cells) by MIT method. The results demonstrated that some of these compounds possessed good antiproliferative activity against the two cancer cell lines. Among them, compound 2c was active against the growth of H1299 lung carcinoma cells with IC50 values of 1.50 mu M, which was more active than the positive topotecan (IC50 = 4.18 mu M). Simultaneously, it showed lower cytotoxic effects on normal NL-20 lung epithelial cells (IC50 > 10 mu M). Mechanism studies indicated that it induced cell cycle arrest at G2/M phase followed by activation of caspase-3, and consequently caused the cell death. Further studies on the structure optimization are ongoing. (C) 2014 Elsevier Masson SAS. All rights reserved.