2-[(E)-3-(4-pyrrolidin-1-ylphenyl)prop-2-enoyl]-3,4-dihydro-2H-naphthalen-1-one

• 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-[(E)-3-(4-pyrrolidin-1-ylphenyl)prop-2-enoyl]-3,4-dihydro-2H-naphthalen-1-one
• 化学式: C₂₃H₂₃NO₂
• 分子量: 345.441
• InChiKey: VOHSVUDQDVZBAO-NTEUORMPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  26
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  37.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2-乙酰-1-四酮 、 4-(1-吡咯啉基)苯甲醛 在 sodium hydroxide 作用下， 以 乙醇 为溶剂， 生成 2-[(E)-3-(4-pyrrolidin-1-ylphenyl)prop-2-enoyl]-3,4-dihydro-2H-naphthalen-1-one
  参考文献：
  名称：

  Biological Activity and Molecular Docking Studies of Curcumin-Related α,β-Unsaturated Carbonyl-Based Synthetic Compounds as Anticancer Agents and Mushroom Tyrosinase Inhibitors

  摘要：

  Hyperpigmentation in human skin and enzymatic browning in fruits, which are caused by tyrosinase enzyme, are not desirable. Investigations in the discovery of tyrosinase enzyme inhibitors and search for improved cytotoxic agents continue to be an important line in drug discovery and development. In present work, a new series of 30 compounds bearing α,β-unsaturated carbonyl moiety was designed and synthesized following curcumin as model. All compounds were evaluated for their effects on human cancer cell lines and mushroom tyrosinase enzyme. Moreover, the structure-activity relationships of these compounds are also explained. Molecular modeling studies of these new compounds were carried out to explore interactions with tyrosinase enzyme. Synthetic curcumin-like compounds (2a-b) were identified as potent anticancer agents with 81-82% cytotoxicity. Five of these newly synthesized compounds (1a, 8a-b, 10a-b) emerged to be the potent inhibitors of mushroom tyrosinase, providing further insight into designing compounds useful in fields of food, health, and agriculture.

  DOI：

  10.1021/jf501145b