1,7-bis[3-hydroxy-4-(2,3,4,6-tetraacetyl-β-D-glucopyranos-1-yloxy)phenyl]hepta-1,6-diene-3,5-dione | 1159278-15-5

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: 1,7-bis[3-hydroxy-4-(2,3,4,6-tetraacetyl-β-D-glucopyranos-1-yloxy)phenyl]hepta-1,6-diene-3,5-dione
• CAS: 1159278-15-5
• 化学式: C₄₇H₅₂O₂₄
• 分子量: 1000.92
• InChiKey: NUHIBDNGMJOPGD-IRCDKXGISA-N

物化性质

• 沸点：
  988.6±65.0 °C(predicted)
• 密度：
  1.42±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.28
• 重原子数：
  71.0
• 可旋转键数：
  20.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  321.92
• 氢给体数：
  2.0
• 氢受体数：
  24.0

反应信息

• 作为反应物：
  描述：

  1,7-bis[3-hydroxy-4-(2,3,4,6-tetraacetyl-β-D-glucopyranos-1-yloxy)phenyl]hepta-1,6-diene-3,5-dione 在 甲醇 、 sodium methylate 作用下， 反应 2.0h， 以100%的产率得到1,7-bis[3-hydroxy-4-(β-D-glucopyranos-1-yloxy)phenyl]hepta-1,6-diene-3,5-dione
  参考文献：
  名称：

  Synthesis, cytotoxic and combined cDDP activity of new stable curcumin derivatives

  摘要：

  New curcumin derivatives are synthesized in order to improve chemical properties of curcumin. The aromatic ring glycosylation of curcumin provides more water-soluble compounds with a greater kinetic stability which is a fundamental feature for drug bioavailability. The glycosylation reaction is quite simple, low cost, with high yield and minimum waste. NMR data show that the ability of curcumin to coordinate metal ion, in particular Ga(III), is maintained in the synthesized products. Although the binding of glucose to curcumin reduces the cytotoxicity of the derivatives towards cisplatin (cDDP)-sensitive and -resistant human ovarian carcinoma cell lines, the compounds display a good selectivity since they are much less toxic against non-tumourigenic Vero cells. The combination of cDDP with the most active glycosyl-curcuminoid drug against both cDDP-sensitive and -resistant as well as against Vero cell lines is tested. The results show an improvement of cDDP efficacy with higher selectivity towards cancer cells than non-cancer cells. These studies indicate the need for developing new valid components of drug treatment protocols to cDDP-resistant cells as well. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2009.03.016
• 作为产物：
  描述：

  2-hydroxy-4-formylphenyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside 、 乙酰丙酮 在 boron trioxide 、 硼酸三丁酯 、 正丁胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 6.0h， 以91%的产率得到1,7-bis[3-hydroxy-4-(2,3,4,6-tetraacetyl-β-D-glucopyranos-1-yloxy)phenyl]hepta-1,6-diene-3,5-dione
  参考文献：
  名称：

  Synthesis, cytotoxic and combined cDDP activity of new stable curcumin derivatives

  摘要：

  New curcumin derivatives are synthesized in order to improve chemical properties of curcumin. The aromatic ring glycosylation of curcumin provides more water-soluble compounds with a greater kinetic stability which is a fundamental feature for drug bioavailability. The glycosylation reaction is quite simple, low cost, with high yield and minimum waste. NMR data show that the ability of curcumin to coordinate metal ion, in particular Ga(III), is maintained in the synthesized products. Although the binding of glucose to curcumin reduces the cytotoxicity of the derivatives towards cisplatin (cDDP)-sensitive and -resistant human ovarian carcinoma cell lines, the compounds display a good selectivity since they are much less toxic against non-tumourigenic Vero cells. The combination of cDDP with the most active glycosyl-curcuminoid drug against both cDDP-sensitive and -resistant as well as against Vero cell lines is tested. The results show an improvement of cDDP efficacy with higher selectivity towards cancer cells than non-cancer cells. These studies indicate the need for developing new valid components of drug treatment protocols to cDDP-resistant cells as well. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2009.03.016