(2E)-N-(2-aminophenyl)-3-(4-{2-[(3,4-dichlorophenyl)amino]-2-oxoethoxy}-3-methoxyphenyl)acrylamide

• 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: (2E)-N-(2-aminophenyl)-3-(4-{2-[(3,4-dichlorophenyl)amino]-2-oxoethoxy}-3-methoxyphenyl)acrylamide
• 英文别名: (E)-N-(2-aminophenyl)-3-[4-[2-(3,4-dichloroanilino)-2-oxoethoxy]-3-methoxyphenyl]prop-2-enamide
• 化学式: C₂₄H₂₁Cl₂N₃O₄
• 分子量: 486.354
• InChiKey: ANHWKFPZTFBNJP-YRNVUSSQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  33
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  103
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  阿魏酸 在 potassium carbonate 、 三氟乙酸 作用下， 以 四氢呋喃 、 丙酮 为溶剂， 反应 27.5h， 生成 (2E)-N-(2-aminophenyl)-3-(4-{2-[(3,4-dichlorophenyl)amino]-2-oxoethoxy}-3-methoxyphenyl)acrylamide
  参考文献：
  名称：

  Development of novel ferulic acid derivatives as potent histone deacetylase inhibitors

  摘要：

  Histone deacetylase inhibitors (HDACIs) offer a promising strategy for cancer therapy. The discovery of potent ferulic acid-based HDACIs with hydroxamic acid or 2-aminobenzamide group as zinc binding group was reported. The halogeno-acetanilide was introduced as novel surface recognition moiety (SRM). The majority of title compounds displayed potent HDAC inhibitory activity. In particular, FA6 and FA16 exhibited significant enzymatic inhibitory activities, with IC50 values of 3.94 and 2.82 mu M, respectively. Furthermore, these compounds showed moderate antiproliferative activity against a panel of human cancer cells. FA17 displayed promising profile as an antitumor candidate. The results indicated that these ferulic acid derivatives could serve as promising lead compounds for further optimization. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2013.09.021

文献信息

• Development of novel ferulic acid derivatives as potent histone deacetylase inhibitors
  作者：Fang Wang、Wen Lu、Tao Zhang、Jinyun Dong、Hongping Gao、Pengfei Li、Sicen Wang、Jie Zhang

  DOI：10.1016/j.bmc.2013.09.021

  日期：2013.11

  Histone deacetylase inhibitors (HDACIs) offer a promising strategy for cancer therapy. The discovery of potent ferulic acid-based HDACIs with hydroxamic acid or 2-aminobenzamide group as zinc binding group was reported. The halogeno-acetanilide was introduced as novel surface recognition moiety (SRM). The majority of title compounds displayed potent HDAC inhibitory activity. In particular, FA6 and FA16 exhibited significant enzymatic inhibitory activities, with IC50 values of 3.94 and 2.82 mu M, respectively. Furthermore, these compounds showed moderate antiproliferative activity against a panel of human cancer cells. FA17 displayed promising profile as an antitumor candidate. The results indicated that these ferulic acid derivatives could serve as promising lead compounds for further optimization. (C) 2013 Elsevier Ltd. All rights reserved.