(E)-3-[4-(2-anilino-2-oxoethoxy)-3-methoxyphenyl]prop-2-enoic acid

• 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: (E)-3-[4-(2-anilino-2-oxoethoxy)-3-methoxyphenyl]prop-2-enoic acid
• 化学式: C₁₈H₁₇NO₅
• 分子量: 327.3
• InChiKey: XHVKTDRQOZEKGX-CSKARUKUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  24
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  84.9
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  香草醛 、 2-氯乙酰苯胺 在 哌啶 、 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 21.0h， 生成 (E)-3-[4-(2-anilino-2-oxoethoxy)-3-methoxyphenyl]prop-2-enoic acid
  参考文献：
  名称：

  Structure-based Drug Design of New Cinnamic Acid Derivatives as Tyrosinase Inhibitors

  摘要：

  Tyrosinase is a critical enzyme responsible for pigmentation disorders, and tyrosinase inhibition is an established strategy to treat hyperpigmentation. In the current study, cinnamic acidbased derivatives were designed and synthesized. All synthesized compounds were confirmed using IR, 1HNMR, 13CNMR, and CNH analysis. The inhibitory potencies of all derivatives against tyrosinase were determined, and it was shown that 5m bearing para-chloro moiety exhibits an IC50 value of 77.62 μmol/L. Analysis of enzyme kinetic studies revealed that 5m is an uncompetitive inhibitor. In silico studies against tyrosinase predicted possible binding mode in the pocket such that 5m formed critical interactions with both Cu co-factors within the binding site. This study presents the potential of aryl-substituted cinnamic acids that can benefit various cosmetic formulations as depigmentation agents.

  DOI：

  10.2174/0115701786263337231227113513