phenethyl (E)-3-(3,4,5-trihydroxyphenyl)prop-2-enoate

• 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: phenethyl (E)-3-(3,4,5-trihydroxyphenyl)prop-2-enoate
• 英文别名: 2-phenylethyl (E)-3-(3,4,5-trihydroxyphenyl)prop-2-enoate
• 化学式: C₁₇H₁₆O₅
• 分子量: 300.311
• InChiKey: COUZOAATCDRXRK-VOTSOKGWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  22
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  87
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  3,4,5-三羟基苯甲醛 、 (carboxymethyl)-triphenylphosphonium chloride, β-phenylethyl ester 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以8%的产率得到phenethyl (E)-3-(3,4,5-trihydroxyphenyl)prop-2-enoate
  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