(2E)-3-[3-(2-{[3-bromo-5-(trifluoromethyl)phenyl]amino}-2-oxoethoxy)-4-methoxyphenyl]-N-hydroxyacrylamide | 1607457-04-4

• 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)-3-[3-(2-{[3-bromo-5-(trifluoromethyl)phenyl]amino}-2-oxoethoxy)-4-methoxyphenyl]-N-hydroxyacrylamide
• 英文别名: (E)-3-[3-[2-[3-bromo-5-(trifluoromethyl)anilino]-2-oxoethoxy]-4-methoxyphenyl]-N-hydroxyprop-2-enamide
• CAS: 1607457-04-4
• 化学式: C₁₉H₁₆BrF₃N₂O₅
• 分子量: 489.246
• InChiKey: DVHUJOYQKXIKIX-HWKANZROSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  30
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.16
• 拓扑面积：
  96.9
• 氢给体数：
  3
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  异阿魏酸 在 羟胺钾盐 、 硫酸 、 羟胺 、 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 反应 38.5h， 生成 (2E)-3-[3-(2-{[3-bromo-5-(trifluoromethyl)phenyl]amino}-2-oxoethoxy)-4-methoxyphenyl]-N-hydroxyacrylamide
  参考文献：
  名称：

  Search for novel histone deacetylase inhibitors. Part II: Design and synthesis of novel isoferulic acid derivatives

  摘要：

  Previously, we described the discovery of potent ferulic acid-based histone deacetylase inhibitors (HDACIs) with halogeno-acetanilide as novel surface recognition moiety (SRM). In order to improve the affinity and activity of these HDACIs, twenty seven isoferulic acid derivatives were described herein. The majority of title compounds displayed potent HDAC inhibitory activity. In particular, IF5 and IF6 exhibited significant enzymatic inhibitory activities, with IC50 values of 0.73 +/- 0.08 and 0.57 +/- 0.16 mu M, respectively. Furthermore, these compounds showed moderate antiproliferative activity against human cancer cells. Especially, IF6 displayed promising profile as an antitumor candidate with IC50 value of 3.91 +/- 0.97 mu M against HeLa cells. The results indicated that these isoferulic acid derivatives could serve as promising lead compounds for further optimization. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2014.03.019

文献信息

• Search for novel histone deacetylase inhibitors. Part II: Design and synthesis of novel isoferulic acid derivatives
  作者：Wen Lu、Fang Wang、Tao Zhang、Jinyun Dong、Hongping Gao、Ping Su、Yaling Shi、Jie Zhang

  DOI：10.1016/j.bmc.2014.03.019

  日期：2014.5

  Previously, we described the discovery of potent ferulic acid-based histone deacetylase inhibitors (HDACIs) with halogeno-acetanilide as novel surface recognition moiety (SRM). In order to improve the affinity and activity of these HDACIs, twenty seven isoferulic acid derivatives were described herein. The majority of title compounds displayed potent HDAC inhibitory activity. In particular, IF5 and IF6 exhibited significant enzymatic inhibitory activities, with IC50 values of 0.73 +/- 0.08 and 0.57 +/- 0.16 mu M, respectively. Furthermore, these compounds showed moderate antiproliferative activity against human cancer cells. Especially, IF6 displayed promising profile as an antitumor candidate with IC50 value of 3.91 +/- 0.97 mu M against HeLa cells. The results indicated that these isoferulic acid derivatives could serve as promising lead compounds for further optimization. (C) 2014 Elsevier Ltd. All rights reserved.