[(2R,3R,4S,5R,6R)-3,4,5-triacetyloxy-6-[2-[4,6-bis[(E)-2-(3,4-dimethoxyphenyl)ethenyl]pyrimidin-2-yl]oxyethoxy]oxan-2-yl]methyl acetate | 1413441-89-0

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮
• 英文名称: [(2R,3R,4S,5R,6R)-3,4,5-triacetyloxy-6-[2-[4,6-bis[(E)-2-(3,4-dimethoxyphenyl)ethenyl]pyrimidin-2-yl]oxyethoxy]oxan-2-yl]methyl acetate
• CAS: 1413441-89-0
• 化学式: C₄₀H₄₆N₂O₁₅
• 分子量: 794.81
• InChiKey: QRWWMRUGRHGPOW-CWRJXISUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  57
• 可旋转键数：
  22
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  196
• 氢给体数：
  0
• 氢受体数：
  17

反应信息

• 作为反应物：
  描述：

  [(2R,3R,4S,5R,6R)-3,4,5-triacetyloxy-6-[2-[4,6-bis[(E)-2-(3,4-dimethoxyphenyl)ethenyl]pyrimidin-2-yl]oxyethoxy]oxan-2-yl]methyl acetate 在 甲醇 、 sodium methylate 作用下， 反应 3.0h， 以83.7%的产率得到(2R,3R,4S,5S,6R)-2-[2-[4,6-bis[(E)-2-(3,4-dimethoxyphenyl)ethenyl]pyrimidin-2-yl]oxyethoxy]-6-(hydroxymethyl)oxane-3,4,5-triol
  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
• 作为产物：
  描述：

  3,4-二甲氧基苯甲醛 在 盐酸 、 四丁基溴化铵 作用下， 以 乙醇 、 氯仿 、 水 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 48.0h， 生成 [(2R,3R,4S,5R,6R)-3,4,5-triacetyloxy-6-[2-[4,6-bis[(E)-2-(3,4-dimethoxyphenyl)ethenyl]pyrimidin-2-yl]oxyethoxy]oxan-2-yl]methyl acetate
  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