methyl (2E)-3-(3-{2-[3,5-bis(trifluoromethyl)phenyl]amino-2-oxoethoxy}-4-methoxyphenyl)acrylate | 1607457-43-1

• 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: methyl (2E)-3-(3-{2-[3,5-bis(trifluoromethyl)phenyl]amino-2-oxoethoxy}-4-methoxyphenyl)acrylate
• CAS: 1607457-43-1
• 化学式: C₂₁H₁₇F₆NO₅
• 分子量: 477.36
• InChiKey: XSQFJXVGHLVFHO-GQCTYLIASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.94
• 重原子数：
  33.0
• 可旋转键数：
  7.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  73.86
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  methyl (2E)-3-(3-{2-[3,5-bis(trifluoromethyl)phenyl]amino-2-oxoethoxy}-4-methoxyphenyl)acrylate 在 羟胺钾盐 、 羟胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 以49.7%的产率得到(2E)-3-[3-(2-{[3,5-bis(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
• 作为产物：
  描述：

  异阿魏酸 在 硫酸 、 potassium carbonate 作用下， 以 丙酮 为溶剂， 反应 14.5h， 生成 methyl (2E)-3-(3-{2-[3,5-bis(trifluoromethyl)phenyl]amino-2-oxoethoxy}-4-methoxyphenyl)acrylate
  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