4,6-bis((E)-3,4,5-trimethoxystyryl)-N-propylpyrimidin-2-amine | 1450593-08-4

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二芳基庚烷
• 英文名称: 4,6-bis((E)-3,4,5-trimethoxystyryl)-N-propylpyrimidin-2-amine
• 英文别名: N-propyl-4,6-bis[(E)-2-(3,4,5-trimethoxyphenyl)ethenyl]pyrimidin-2-amine
• CAS: 1450593-08-4
• 化学式: C₂₉H₃₅N₃O₆
• 分子量: 521.613
• InChiKey: KJNGAODYGUHCCJ-WGDLNXRISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  38
• 可旋转键数：
  13
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  93.2
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为产物：
  描述：

  4,6-二甲基-2-羟基嘧啶盐酸盐 在 盐酸 、 N,N-二异丙基乙胺 、 三氯氧磷 作用下， 以 乙醇 、 水 、 甲苯 为溶剂， 反应 14.0h， 生成 4,6-bis((E)-3,4,5-trimethoxystyryl)-N-propylpyrimidin-2-amine
  参考文献：
  名称：

  Exploring pyrimidine-substituted curcumin analogues: Design, synthesis and effects on EGFR signaling

  摘要：

  Epidermal growth factor receptor (EGFR) is an effective molecular target of anti-cancer therapies. Curcumin inhibits cancer cell growth in vitro by suppressing gene expression of EGFR and reduces tumor growth in various animal models. To overcome instable and insoluble properties of curcumin as therapeutics, we designed and synthesized six novel pyrimidine-substituted curcumin analogues with or without a hydroxyl group originally present in curcumin. The cell viability tests indicated that IC50 of the analogues containing hydroxyl group were 3 to 8-fold lower than those of the analogues without hydroxyl group in two colon cancer cell lines tested. Western blot analysis indicates the analogues containing hydroxyl group inhibited expression and tyrosine phosphorylation of EGFR. Further protein analyses showed that the analogues had anti-cellular proliferation, pro-apoptosis, and cell cycle arrest properties associated with suppressed EGFR expression. These results indicate that the hydroxyl groups in curcumin and the analogues were critical for observed biological activities. (C) 2013 The Authors. Published by Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2013.06.053

文献信息

• Exploring pyrimidine-substituted curcumin analogues: Design, synthesis and effects on EGFR signaling
  作者：Peiju Qiu、Lingling Xu、Lei Gao、Meng Zhang、Shixi Wang、Sheng Tong、Yue Sun、Lijuan Zhang、Tao Jiang

  DOI：10.1016/j.bmc.2013.06.053

  日期：2013.9

  Epidermal growth factor receptor (EGFR) is an effective molecular target of anti-cancer therapies. Curcumin inhibits cancer cell growth in vitro by suppressing gene expression of EGFR and reduces tumor growth in various animal models. To overcome instable and insoluble properties of curcumin as therapeutics, we designed and synthesized six novel pyrimidine-substituted curcumin analogues with or without a hydroxyl group originally present in curcumin. The cell viability tests indicated that IC50 of the analogues containing hydroxyl group were 3 to 8-fold lower than those of the analogues without hydroxyl group in two colon cancer cell lines tested. Western blot analysis indicates the analogues containing hydroxyl group inhibited expression and tyrosine phosphorylation of EGFR. Further protein analyses showed that the analogues had anti-cellular proliferation, pro-apoptosis, and cell cycle arrest properties associated with suppressed EGFR expression. These results indicate that the hydroxyl groups in curcumin and the analogues were critical for observed biological activities. (C) 2013 The Authors. Published by Elsevier Ltd. All rights reserved.