(E)-1-(2-hydroxy-4,6-dimethoxyphenyl)-3-(2,3,4-trimethoxyphenyl)prop-2-en-1-one

• 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: (E)-1-(2-hydroxy-4,6-dimethoxyphenyl)-3-(2,3,4-trimethoxyphenyl)prop-2-en-1-one
• 化学式: C₂₀H₂₂O₇
• 分子量: 374.39
• InChiKey: DLXWWGUSWDUAEV-SOFGYWHQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  27
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  83.4
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  2-羟基-4,6-二甲氧基苯乙酮 、 2,3,4-三甲氧基苯甲醛 在 氢氧化钾 作用下， 以 乙醇 为溶剂， 反应 48.0h， 以85%的产率得到(E)-1-(2-hydroxy-4,6-dimethoxyphenyl)-3-(2,3,4-trimethoxyphenyl)prop-2-en-1-one
  参考文献：
  名称：

  Differential effects of synthesized 2′-oxygenated chalcone derivatives: modulation of human cell cycle phase distribution

  摘要：

  Ten structurally related T-oxygenated chalcone derivatives, bearing either hydroxy and/or methoxy substituents oil the A and B rings, were synthesized through Claisen-Schmidt condensation. The synthesis procedure was relatively easy and had an acceptable yield. The in vitro cytotoxicities of these compounds against the human tumor cells such as Jurkat, U937 cells, and normal cells PHA stimulated PBMCs were investigated. Among those, compounds 1 (IC50 = 2.5 muM), 2 (1.7 muM), and 8 (3.2 muM) showed potent inhibitory activity toward Jurkat cell line. In parallel, compounds 1 (6.7 muM), 2 (1.5 muM), and 10 (5.3 muM) showed the highest activity against U937 cell line. However, the chalcones also inhibit the PHA stimulated PBMCs cells, but the IC50 values were relatively high when compared to the tumor cell line values. Studies were also on the effect of synthesized chalcones on the cell cycle phase distribution. In Jurkat cell line, compounds 7 and 9 showed the highest activity and the most striking effect in reduction of the percentage of cells in the S phase, which was associated with an increase of cells in G2/M phase. In U937 cell line, compound 3 increased the proportion of cells in the G0/G1 phase and reduced the proportion in S phase. In contrast, compounds 1, 9, and 10 showed a decrease effect on the percentage of cells in S phase and an increase effect on the percentage of cells in the G2/M phase of the cell cycle. Whereas in the case of PHA stimulated PBMCs, compounds 1, 4, 8, and 10 increased the percentage of cells in G2/M phase, which was associated with a decrease effect in the :S phase of the cell cycle. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2004.03.014