3-((4-ethoxycarbonyloxy)-3-methoxyphenyl)acrylic acid | 42381-67-9

• 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: 3-((4-ethoxycarbonyloxy)-3-methoxyphenyl)acrylic acid
• 英文别名: 3-{4-[(Ethoxycarbonyl)oxy]-3-methoxyphenyl}prop-2-enoic acid；3-(4-ethoxycarbonyloxy-3-methoxyphenyl)prop-2-enoic acid
• CAS: 42381-67-9
• 化学式: C₁₃H₁₄O₆
• 分子量: 266.251
• InChiKey: FHJHNBRYOKQMEJ-UHFFFAOYSA-N

物化性质

• 沸点：
  446.1±45.0 °C(Predicted)
• 密度：
  1.270±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  19
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  82.1
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  3-((4-ethoxycarbonyloxy)-3-methoxyphenyl)acrylic acid 在 草酰氯 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 生成 4-(3-chloro-3-oxoprop-1-enyl)-2-methoxylphenyl ethyl carbonate
  参考文献：
  名称：

  Ferulic acid–carbazole hybrid compounds: Combination of cholinesterase inhibition, antioxidant and neuroprotection as multifunctional anti-Alzheimer agents

  摘要：

  In order to search for novel multifunctional anti-Alzheimer agents, a series of ferulic acid-carbazole hybrid compounds were designed and synthesized. Ellman's assay revealed that the hybrid compounds showed moderate to potent inhibitory activity against the cholinesterases. Particularly, the AChE inhibition potency of compound 5k (IC50 1.9 mu M) was even 5-fold higher than that of galantamine. In addition, the target compounds showed pronounced antioxidant ability and neuroprotective property, especially against the ROS-induced toxicity. Notably, the neuroprotective effect of 5k was obviously superior to that of the mixture of ferulic acid and carbazole, indicating the therapeutic effect of the hybrid compound is better than the combination administration of the corresponding mixture. (c) 2016 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2016.01.010
• 作为产物：
  描述：

  阿魏酸 、 氯甲酸乙酯 在 sodium hydroxide 作用下， 生成 3-((4-ethoxycarbonyloxy)-3-methoxyphenyl)acrylic acid
  参考文献：
  名称：

  阿魏酸和咖啡酸衍生物的生物活性评估和构效关系分析

  摘要：

  通过高通量筛选（HTS）方法评估了烷基酯和阿魏酸（FA）和咖啡酸（CA）的NO供体的抗癌活性，并描述了结构与活性之间的关系。与具有相同烷基取代基的FA烷基酯相比，CA烷基酯具有更好的抗癌活性。单硝酸盐和苯基呋喃喃硝酸盐比双硝酸盐更有效。FA的苯磺酰呋喃呋喃硝酸盐，尤其是化合物8b - 8d在抗癌方面表现出更强的活性。

  DOI：

  10.1016/j.bmcl.2012.08.038

文献信息

• Ferulic acid–carbazole hybrid compounds: Combination of cholinesterase inhibition, antioxidant and neuroprotection as multifunctional anti-Alzheimer agents
  作者：Lei Fang、Mohao Chen、Zhikun Liu、Xubin Fang、Shaohua Gou、Li Chen

  DOI：10.1016/j.bmc.2016.01.010

  日期：2016.2

  In order to search for novel multifunctional anti-Alzheimer agents, a series of ferulic acid-carbazole hybrid compounds were designed and synthesized. Ellman's assay revealed that the hybrid compounds showed moderate to potent inhibitory activity against the cholinesterases. Particularly, the AChE inhibition potency of compound 5k (IC50 1.9 mu M) was even 5-fold higher than that of galantamine. In addition, the target compounds showed pronounced antioxidant ability and neuroprotective property, especially against the ROS-induced toxicity. Notably, the neuroprotective effect of 5k was obviously superior to that of the mixture of ferulic acid and carbazole, indicating the therapeutic effect of the hybrid compound is better than the combination administration of the corresponding mixture. (c) 2016 Elsevier Ltd. All rights reserved.
• Biological activity evaluation and structure–activity relationships analysis of ferulic acid and caffeic acid derivatives for anticancer
  作者：Weixia Li、Nianguang Li、Yuping Tang、Baoquan Li、Li Liu、Xu Zhang、Haian Fu、Jin-ao Duan

  DOI：10.1016/j.bmcl.2012.08.038

  日期：2012.10

  The anticancer activities of alkyl esters and NO-donors of ferulic acid (FA) and caffeic acid (CA) were assessed by a high-throughout screening (HTS) method, and the structure–activity relationships were described. CA alkyl esters had better anticancer activities than FA alkyl esters with the same alkyl substituent. Mono-nitrates and phenylfuroxan nitrates were more potent than the dual nitrates.

  通过高通量筛选（HTS）方法评估了烷基酯和阿魏酸（FA）和咖啡酸（CA）的NO供体的抗癌活性，并描述了结构与活性之间的关系。与具有相同烷基取代基的FA烷基酯相比，CA烷基酯具有更好的抗癌活性。单硝酸盐和苯基呋喃喃硝酸盐比双硝酸盐更有效。FA的苯磺酰呋喃呋喃硝酸盐，尤其是化合物8b - 8d在抗癌方面表现出更强的活性。