diethyl (5-(benzyloxy)-4-oxo-4H-pyran-2-yl)methylphosphonate | 1381864-85-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃
• 英文名称: diethyl (5-(benzyloxy)-4-oxo-4H-pyran-2-yl)methylphosphonate
• CAS: 1381864-85-2
• 化学式: C₁₇H₂₁O₆P
• 分子量: 352.324
• InChiKey: XKJXUHRBDREREI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.98
• 重原子数：
  24.0
• 可旋转键数：
  9.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  74.97
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  diethyl (5-(benzyloxy)-4-oxo-4H-pyran-2-yl)methylphosphonate 在 三溴化硼 、 sodium hydride 作用下， 以 四氢呋喃 、 二氯甲烷 、 mineral oil 为溶剂， 反应 25.0h， 生成 (E)-2-(3,4-dihydroxystyryl)-5-hydroxy-4H-pyran-4-one
  参考文献：
  名称：

  Synthesis of kojic acid-derived copper-chelating apoptosis inducing agents

  摘要：

  Three classes of kojic acid derivatives were synthesized and examined for their antiproliferative activity against HeLa cells. Both 8b and 11 co-treated with copper ion exhibited synergistic effect on the HeLa cell growth inhibition with GI(50) values of 11.9 and 7.1 mu M, respectively. Flow cytometric analysis of HeLa cells revealed that 11-Cu co-treatment induced the sub-G1 arrest in a dose-dependent manner, suggesting that the growth-inhibitory effect is attributed to DNA fragmentation. Moreover, western blot of HeLa cells cytosolic extracts displayed the cleavage of the 116-kDa protein poly(ADP-ribose) polymerase and activation of caspase-3 by the reduced level of the 32-kDa proenzyme, indicating that the caspase-dependent apoptotic pathway was involved. We further demonstrated that MAPK pathway regulators such as ERK and p38 were activated in response to 11-Cu co-treatment, suggesting that the intracellular oxidative stress was dramatically stimulated by the copper ion. Taken together, we have successfully synthesized kojic acid-derived copper-induced apoptotic agents.

  DOI：

  10.1007/s00044-012-0094-y
• 作为产物：
  描述：

  溴甲苯 在 potassium carbonate 、 三乙胺 、 sodium bromide 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 26.5h， 生成 diethyl (5-(benzyloxy)-4-oxo-4H-pyran-2-yl)methylphosphonate
  参考文献：
  名称：

  Synthesis of kojic acid-derived copper-chelating apoptosis inducing agents

  摘要：

  Three classes of kojic acid derivatives were synthesized and examined for their antiproliferative activity against HeLa cells. Both 8b and 11 co-treated with copper ion exhibited synergistic effect on the HeLa cell growth inhibition with GI(50) values of 11.9 and 7.1 mu M, respectively. Flow cytometric analysis of HeLa cells revealed that 11-Cu co-treatment induced the sub-G1 arrest in a dose-dependent manner, suggesting that the growth-inhibitory effect is attributed to DNA fragmentation. Moreover, western blot of HeLa cells cytosolic extracts displayed the cleavage of the 116-kDa protein poly(ADP-ribose) polymerase and activation of caspase-3 by the reduced level of the 32-kDa proenzyme, indicating that the caspase-dependent apoptotic pathway was involved. We further demonstrated that MAPK pathway regulators such as ERK and p38 were activated in response to 11-Cu co-treatment, suggesting that the intracellular oxidative stress was dramatically stimulated by the copper ion. Taken together, we have successfully synthesized kojic acid-derived copper-induced apoptotic agents.

  DOI：

  10.1007/s00044-012-0094-y