4-dimethylamino-4'-acetamidochalcone

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 英文名称: 4-dimethylamino-4'-acetamidochalcone
• 英文别名: N-[4-[3-[4-(dimethylamino)phenyl]prop-2-enoyl]phenyl]acetamide
• 化学式: C₁₉H₂₀N₂O₂
• mdl: MFCD00746051
• 分子量: 308.38
• InChiKey: PNSVICPSMTUZNX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.16
• 拓扑面积：
  49.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  对二甲氨基苯甲醛 、 4-乙酰胺苯乙酮 在 sodium hydroxide 作用下， 以 乙醇 为溶剂， 反应 48.0h， 以30%的产率得到4-dimethylamino-4'-acetamidochalcone
  参考文献：
  名称：

  Design, synthesis and bioactivity of chalcones and its analogues

  摘要：

  The Vernohia anthelmintica L's extract is one of the most popular Uygur medicines used for vitiligo. It is believed that the chalcone compounds of the plant play an important role in the treatment since they may activate tyrosinase and improve melanin production. In this study, twenty-one chalcones and nine analogues were synthesized in view of three different components of chalcone (A, B ring and a, beta-unsaturated carbonyl). After biological evaluation of their activity on tyrosinase in cell-free systems, the result showed that most compounds (except polyhydroxy chalcones) possess activator effect on the tyrosinase, especially for 13a-15a, 20a and 1 b, which bearing a comparable activity to the positive control 8-MOP. SAR of these tyrosinase activator was summed up for the first time as well. Finally, compound 13a was found to increase melanin contents and tyrosinase activity 1.75 and 1.3 fold, respectively, compared with that of untreated murine B16 cells at the concentration of 40 mu g/mL (C) 2017 Chinese Chemical Society and Institute of Materia Medica, Chinese Academy of Medical Sciences. Published by Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.cclet.2017.03.018

文献信息

• Design, synthesis and bioactivity of chalcones and its analogues
  作者：Chao Niu、Adila Tuerxuntayi、Gen Li、Madina Kabas、Chang-Zhi Dong、Haji Akber Aisa

  DOI：10.1016/j.cclet.2017.03.018

  日期：2017.7

  The Vernohia anthelmintica L's extract is one of the most popular Uygur medicines used for vitiligo. It is believed that the chalcone compounds of the plant play an important role in the treatment since they may activate tyrosinase and improve melanin production. In this study, twenty-one chalcones and nine analogues were synthesized in view of three different components of chalcone (A, B ring and a, beta-unsaturated carbonyl). After biological evaluation of their activity on tyrosinase in cell-free systems, the result showed that most compounds (except polyhydroxy chalcones) possess activator effect on the tyrosinase, especially for 13a-15a, 20a and 1 b, which bearing a comparable activity to the positive control 8-MOP. SAR of these tyrosinase activator was summed up for the first time as well. Finally, compound 13a was found to increase melanin contents and tyrosinase activity 1.75 and 1.3 fold, respectively, compared with that of untreated murine B16 cells at the concentration of 40 mu g/mL (C) 2017 Chinese Chemical Society and Institute of Materia Medica, Chinese Academy of Medical Sciences. Published by Elsevier B.V. All rights reserved.