(E,E)-4,6-bis(4-methoxystyryl)-2-D-glucopyranosyloxy-pyrimidine | 1413441-82-3

• 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: (E,E)-4,6-bis(4-methoxystyryl)-2-D-glucopyranosyloxy-pyrimidine
• 英文别名: (2S,3R,4S,5S,6R)-2-[4,6-bis[(E)-2-(4-methoxyphenyl)ethenyl]pyrimidin-2-yl]oxy-6-(hydroxymethyl)oxane-3,4,5-triol
• CAS: 1413441-82-3
• 化学式: C₂₈H₃₀N₂O₈
• 分子量: 522.555
• InChiKey: FSTJAKFZRPEQRL-LUVANHNFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  38
• 可旋转键数：
  9
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  144
• 氢给体数：
  4
• 氢受体数：
  10

反应信息

• 作为产物：
  描述：

  4-甲氧基苯甲醛 在 盐酸 、 甲醇 、 四丁基溴化铵 、 sodium methylate 作用下， 以 乙醇 、 氯仿 、 水 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 51.0h， 生成 (E,E)-4,6-bis(4-methoxystyryl)-2-D-glucopyranosyloxy-pyrimidine
  参考文献：
  名称：

  Synthesis of a Novel Series of (E,E)-4,6-bis(styryl)-2-O-Glucopyranosyl-Pyrimidines and Their Potent Multidrug Resistance (MDR) Reversal Activity Against Cancer Cells

  摘要：

  A novel series of methoxy or benzyloxy substituted (E,E)-4,6-bis(styryl)-2-O-glucopyranosyl-pyrimidines as curcuminoid analogs were synthesized in four steps with total yields of 21.5% to 33.9%. A549 and HL60 cells were employed for the anticancer activity testing. The results demonstrated that 5a, 5c, and 5e have some inhibitory activity against the HL-60 cell line. Unfortunately, no compound displayed inhibitory activity against A549 except for 5c. MDR reversal activity results demonstrated that compounds 4a (RF = 12.3) and 4b (RF = 18.5) showed strong reversal activity to the P-gp-mediated LCC6MDR cells compared to verapamil (RF = 3.2) and no cytotoxicity to cancer or normal cell lines even at a high concentrations (100 mu M).

  DOI：

  10.1080/07328303.2012.689041

文献信息

• Synthesis of a Novel Series of (<i>E</i>,<i>E</i>)-4,6-bis(styryl)-2-<i>O</i>-Glucopyranosyl-Pyrimidines and Their Potent Multidrug Resistance (MDR) Reversal Activity Against Cancer Cells
  作者：Lei Gao、Qian Liu、Sumei Ren、Shengbiao Wan、Tao Jiang、Iris L. K. Wong、Larry M. C. Chow、Shixi Wang

  DOI：10.1080/07328303.2012.689041

  日期：2012.10

  A novel series of methoxy or benzyloxy substituted (E,E)-4,6-bis(styryl)-2-O-glucopyranosyl-pyrimidines as curcuminoid analogs were synthesized in four steps with total yields of 21.5% to 33.9%. A549 and HL60 cells were employed for the anticancer activity testing. The results demonstrated that 5a, 5c, and 5e have some inhibitory activity against the HL-60 cell line. Unfortunately, no compound displayed inhibitory activity against A549 except for 5c. MDR reversal activity results demonstrated that compounds 4a (RF = 12.3) and 4b (RF = 18.5) showed strong reversal activity to the P-gp-mediated LCC6MDR cells compared to verapamil (RF = 3.2) and no cytotoxicity to cancer or normal cell lines even at a high concentrations (100 mu M).