N-(3,4-dihydroxyhydrocinnamoyl)phenethylamine

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: N-(3,4-dihydroxyhydrocinnamoyl)phenethylamine
• 英文别名: 3-(3,4-dihydroxyphenyl)-N-phenethyl-propanamide；3-(3,4-dihydroxyphenyl)-N-(2-phenylethyl)propanamide
• 化学式: C₁₇H₁₉NO₃
• 分子量: 285.343
• InChiKey: AQPITNHTVNCELU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  21
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  69.6
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  3,4-二羟基苯基丙酸 在 N,N'-二环己基碳二亚胺 作用下， 以 1,4-二氧六环 、 氯仿 为溶剂， 生成 N-(3,4-dihydroxyhydrocinnamoyl)phenethylamine
  参考文献：
  名称：

  Hydroxylated Aromatic Inhibitors of HIV-1 Integrase

  摘要：

  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.

  DOI：

  10.1021/jm00021a006

文献信息

• Mining Plants for Bacterial Quorum Sensing Modulators
  作者：Shimrit David、Aviad Mandabi、Shaked Uzi、Asaph Aharoni、Michael M. Meijler

  DOI：10.1021/acschembio.7b00859

  日期：2018.1.19

  uses quorum sensing (QS) in order to regulate the transfer of DNA into the host plant genome, and this results in the induction of crown gall tumors. The deleterious results of these infections are widespread and affect many species of fruit and crops. In order to further our understanding of this process and to provide potential solutions, we evaluated a library of 3800 natural products from plant

  细菌植物病原体根癌农杆菌使用群体感应（QS）来调节DNA向宿主植物基因组中的转移，从而导致冠状胆囊肿瘤的诱导。这些感染的有害结果广泛存在，并影响许多种类的水果和农作物。为了进一步了解该过程并提供可能的解决方案，我们评估了一个来自植物的3800种天然产物的库，并确定了能够强烈调节植物与细菌相互作用的有效化合物。
• Identification and Quantification of Potential Anti-inflammatory Hydroxycinnamic Acid Amides from Wolfberry
  作者：Siyu Wang、Joon Hyuk Suh、Xi Zheng、Yu Wang、Chi-Tang Ho

  DOI：10.1021/acs.jafc.6b05136

  日期：2017.1.18

  their active components. We synthesized a set of hydroxycinnamic acid amide (HCCA) compounds, including trans-caffeic acid, trans-ferulic acid, and 3,4-dihydroxyhydrocinnamic acid, with extended phenolic amine components as standards to identify and quantify the corresponding compounds from wolfberry and to investigate anti-inflammatory properties of these compounds using in vitro model. With optimized

  枸杞子或枸杞的果枸杞，具有促进健康的特性，导致其有效成分的深入研究。我们合成了一组羟基肉桂酸酰胺（HCCA）化合物，包括反式咖啡酸，反式-阿魏酸和3,4-二羟基氢肉桂酸（含扩展的酚胺成分）作为标准品，用于鉴定和定量枸杞中的相应化合物，并使用体外模型研究这些化合物的抗炎特性。通过优化的LC-MS / MS和NMR分析，从水果中鉴定出9种酰胺化合物。这些化合物中有7种是首次在该植物中鉴定出来的。具有酪胺部分的酰胺化合物最丰富。体外研究表明，5个HCCA化合物显示出对NO产生由脂多糖与IC inuded抑制作用50小于15.08μM（反式- ñ -feruloyl多巴胺）。这些发现表明，枸杞具有抗炎特性。
• 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.