(E)-3-[4-[2-hydroxyethyl(methyl)amino]phenyl]-1-(5-methylfuran-2-yl)prop-2-en-1-one | 1599471-93-8

• 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-hydroxyethyl(methyl)amino]phenyl]-1-(5-methylfuran-2-yl)prop-2-en-1-one
• CAS: 1599471-93-8
• 化学式: C₁₇H₁₉NO₃
• 分子量: 285.343
• InChiKey: BYGHUTNTXPRJQH-RMKNXTFCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 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：
  53.7
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  5-甲基-2-乙酰基呋喃 、 N-甲基-N-(2-羟乙基)-4-氨基苯醛 在 sodium hydroxide 作用下， 以 乙醇 为溶剂， 以32%的产率得到(E)-3-[4-[2-hydroxyethyl(methyl)amino]phenyl]-1-(5-methylfuran-2-yl)prop-2-en-1-one
  参考文献：
  名称：

  Synthesis and Evaluation of Chalcone Derivatives as Inhibitors of Neutrophils' Chemotaxis, Phagocytosis and Production of Reactive Oxygen Species

  摘要：

  Inhibitory effects on neutrophils' chemotaxis, phagocytosis and production of reactive oxygen species (ROS) are among the important targets in developing anti‐inflammatory agents and immunosuppressants. Eight series of chalcone derivatives including five newly synthesized series were assessed for their inhibitory effects on chemotaxis, phagocytosis and ROS production in human polymorphonuclear neutrophils (PMNs). Inhibition of PMNs' chemotaxis and phagocytosis abilities were investigated using the Boyden chamber technique and the Phagotest kit, respectively, while ROS production was evaluated using luminol‐ and lucigenin‐based chemiluminescence assay. The new derivatives (4d and 8d), which contain 4‐methylaminoethanol functional group were active in all the assays performed. It was also observed that some of the compounds were active in inhibiting chemotaxis while others suppressed phagocytosis and ROS production. The information obtained gave new insight into chalcone derivatives with the potential to be developed as immunomodulators.

  DOI：

  10.1111/cbdd.12226

文献信息

• Synthesis and Evaluation of Chalcone Derivatives as Inhibitors of Neutrophils' Chemotaxis, Phagocytosis and Production of Reactive Oxygen Species
  作者：Syed N. A. Bukhari、Yasmin Tajuddin、Vannessa J. Benedict、Kok W. Lam、Ibrahim Jantan、Juriyati Jalil、Malina Jasamai

  DOI：10.1111/cbdd.12226

  日期：2014.2

  Inhibitory effects on neutrophils' chemotaxis, phagocytosis and production of reactive oxygen species (ROS) are among the important targets in developing anti‐inflammatory agents and immunosuppressants. Eight series of chalcone derivatives including five newly synthesized series were assessed for their inhibitory effects on chemotaxis, phagocytosis and ROS production in human polymorphonuclear neutrophils (PMNs). Inhibition of PMNs' chemotaxis and phagocytosis abilities were investigated using the Boyden chamber technique and the Phagotest kit, respectively, while ROS production was evaluated using luminol‐ and lucigenin‐based chemiluminescence assay. The new derivatives (4d and 8d), which contain 4‐methylaminoethanol functional group were active in all the assays performed. It was also observed that some of the compounds were active in inhibiting chemotaxis while others suppressed phagocytosis and ROS production. The information obtained gave new insight into chalcone derivatives with the potential to be developed as immunomodulators.