2-phenylethyl (E)-3-(3,4-dimethoxyphenyl)acrylate

• 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: 2-phenylethyl (E)-3-(3,4-dimethoxyphenyl)acrylate
• 英文别名: 2-phenylethyl (2E)-3-(3,4-dimethoxyphenyl)prop-2-enoate；phenethyl (E)-3-(3,4-dimethoxyphenyl)acrylate；Phenethyl Dimethyl Caffeate；2-phenylethyl (E)-3-(3,4-dimethoxyphenyl)prop-2-enoate
• 化学式: C₁₉H₂₀O₄
• 分子量: 312.365
• InChiKey: OHBFHJOQNCVEOU-PKNBQFBNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  23
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  苯乙醇 、 3,4-二甲氧基肉酸酸 在 4-二甲氨基吡啶 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 以53%的产率得到2-phenylethyl (E)-3-(3,4-dimethoxyphenyl)acrylate
  参考文献：
  名称：

  咖啡酸苯乙酯（CAPE）衍生物充当乙酰胆碱酯酶的选择性抑制剂

  摘要：

  对于新合成的一类咖啡酸苯乙酯（CAPE）衍生物，可能发现对ee AChE的意外抑制作用。因此，苯乙基- （E）-3-（3,5-二甲氧基-4-苯乙氧基苯基）-丙烯酸酯（K i  = 1.97± 0.38μM，K i´  = 2.44± 0.07μM）和4-（2-（（（ë）-3-（3,4-双（苄氧基）苯基）丙烯酰基）氧基）乙基）-1,2-亚苯基（2 ë，2' ë） -双（3-（3,4-双（苯甲氧基） ））（K i  = 0.72±0.31μM，K i´  = 1.80± 0.21μM）对ee的抑制作用非常好AChE对恶性人类癌细胞和非恶性小鼠成纤维细胞无细胞毒性。而且，它们是BChE的弱抑制剂（来自马血清）。

  DOI：

  10.1016/j.ejmech.2019.05.059

文献信息

• A Rapid and Practical Catalytic Esterification for the Preparation of Caffeic Acid Esters
  作者：Dongsheng Xie、Fengzhi Yang、Jin Xie、Man Zhang、Wenlu Liu、Lei Fu

  DOI：10.3184/174751914x14146000527920

  日期：2014.11

  A convenient and practical catalytic method for the preparation of caffeic acid esters is reported. This esterification was carried out with high efficiency in the presence of ytterbium triflate in nitromethane without any other auxiliary reagents. The wide scope of application and especially the higher reactivity and more convenient procedure than previous methods make it a valuable application for the synthesis of caffeic acid esters and other cinnamic acid esters.

  报告中介绍了一种方便实用的催化方法来制备咖啡酸酯。这种酯化反应是在硝基甲烷中三酸镱的存在下高效进行的，无需任何其他辅助试剂。与以前的方法相比，该方法应用范围广，特别是反应活性更高，操作过程更简便，因此在合成咖啡酸酯和其他肉桂酸酯方面具有重要的应用价值。
• Sinapic acid phenethyl ester as a potent selective 5-lipoxygenase inhibitor: Synthesis and structure-activity relationship
  作者：Mohamed Touaibia、Martin J. G. Hébert、Natalie A. Levesque、Jérémie A. Doiron、Marco S. Doucet、Jacques Jean-François、Marc Cormier、Luc H. Boudreau、Marc E. Surette

  DOI：10.1111/cbdd.13360

  日期：2018.11

  inhibitors is highly demanded. The action of several phenolic acid phenethyl esters as potential 5‐Lipoxygenase (5‐LO) inhibitors has been investigated. For this purpose, a series of 14 phenethyl esters was synthesized and their impact on 5‐LO inhibition was evaluated. The effects of position and number of hydroxyl and methoxy groups on the phenolic acid were investigated. The shortening of the linker between

  由于肝毒性和齐留通（Zyflo的不利的药物代谢动力学曲线®），目前唯一批准用于临床5-脂氧合酶（5-LO）抑制剂，有效和安全的5-LO抑制剂的研究是非常需要的。已经研究了几种酚酸苯乙酯作为潜在的5-Lipoxygenase（5-LO）抑制剂的作用。为此目的，合成了一系列14种苯乙酯，并评估了它们对5-LO抑制的影响。研究了羟基和甲氧基的位置和数量对酚酸的影响。还研究了羰基和邻苯二酚部分之间连接基的缩短以及α，β-不饱和羰基的存在。芥子酸苯乙酯（10）（类似于咖啡酸苯乙酯（CAPE））可以命名为SAPE（10），它以浓度依赖的方式抑制5-LO，并且优于zileuton（1）和CAPE（2）。随着集成电路的50 0.3μ的米，SAPE（10）有三个比CAPE（更有效2）和10倍齐留通（更有效1），批准用于临床使用的唯一5-LO抑制剂。与CAPE（2）不同，SAPE（10）对12-脂氧合酶（12
• Hydroxylated Aromatic Inhibitors of HIV-1 Integrase
  作者：Terrence R. Jr. Burke、Mark Fesen、Abhijit Mazumder、Jessie Yung、Jian Wang、Adelaide M. Carothers、Dezider Grunberger、John Driscoll、Yves Pommier、Kurt Kohn

  DOI：10.1021/jm00021a006

  日期：1995.10

  Efficient replication of HIV-1 requires integration of a DNA copy of the viral genome into a chromosome of the host cell. Integration is catalyzed by the viral integrase, and we have previously reported that phenolic moieties in compounds such as flavones, caffeic acid phenethyl ester (CAFE, 2), and curcumin confer inhibitory activity against HIV-1 integrase. We now extend these findings by performing a comprehensive structure-activity relationship using CAPE analogues. Approximately 30 compounds have been prepared as HIV integrase inhibitors based on the structural lead provided by CAPE, which has previously been shown to exhibit an IC50 value of 7 mu M in our integration assay. These analogues were designed to examine specific features of the parent CAFE structure which may be important for activity. Among the features examined for their effects on inhibitory potency were ring substitution, side chain length and composition, and phenyl ring conformational orientation. In an assay which measured the combined effect of two sequential steps, dinucleotide cleavage and strand transfer, several analogues have IC50 values for 3'-processing and strand transfer lower than those of CAFE. Inhibition of strand transfer was assayed using both blunt-ended and ''precleaved'' DNA substrates. Disintegration using an integrase mutant lacking the N-terminal zinc finger and C-terminal DNA-binding domains was also inhibited by these analogues, suggesting that the binding site for these compounds resides in the central catalytic core. Several CAFE analogues were also tested for selective activity against transformed cells. Taken together, these results suggest that the development of novel antiviral agents for the treatment of acquired immune deficiency syndrome can be based upon inhibition of HIV-1 integrase.
• COMBINATION THERAPY
  申请人：Chemigen

  公开号：EP2629766B1

  公开（公告）日：2017-02-22
• METHODS OF TREATING SKIN DISORDERS WITH CAFFEIC ACID ANALOGS
  申请人：CONRAD CHARLES

  公开号：US20080167277A1

  公开（公告）日：2008-07-10

  Methods of treating skin diseases such as plaque psoriasis and inverse psoriasis include topical application of one or a combination of caffeic acid phenethyl ester, caffeic acid benzyl ester, and analogs thereof as an active agent. A pharmaceutical composition containing the active agent may further include a cell differentiating agent such as a retinoid, and/or vitamin D or analogs thereof. The method enables treatment of a lesion with active agent dosages of ten percent by weight, for example.