3,4-dihydro-12-O-(6'-hydroxyhexyl)-2,2-dimethyl-2H,6H-pyrano[3,2-b]xanthen-6-one

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: 3,4-dihydro-12-O-(6'-hydroxyhexyl)-2,2-dimethyl-2H,6H-pyrano[3,2-b]xanthen-6-one
• 英文别名: 4-O-(5-hydroxypentyl)pyranoxanthone；12-(5-Hydroxypentoxy)-2,2-dimethyl-3,4-dihydropyrano[3,2-b]xanthen-6-one；12-(5-hydroxypentoxy)-2,2-dimethyl-3,4-dihydropyrano[3,2-b]xanthen-6-one
• 化学式: C₂₃H₂₆O₅
• 分子量: 382.456
• InChiKey: KNLJDPWSTQRAGI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  28
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  65
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3,4-dihydro-12-O-(6'-hydroxyhexyl)-2,2-dimethyl-2H,6H-pyrano[3,2-b]xanthen-6-one 、 2,5-己酮可可碱 在 4-二甲氨基吡啶 、 N,N'-二环己基碳二亚胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 以48.3%的产率得到3,4-dihydro-2,2-dimethyl-2H,6H-pyrano[3,2-b]xanthen-6-one-12-O-hexyl 5,6-dimethylxanthone-4-acetate
  参考文献：
  名称：

  DMXAA-pyranoxanthone hybrids enhance inhibition activities against human cancer cells with multi-target functions

  摘要：

  Four 5,6-dimethylxanthone-4-acetic acid (D) and pyranoxanthone (P) hybrids (D-P-n) were design-synthesized based on multi-target-addressed strategy. D-P-4 was confirmed as the most active agent against HepG-2 cell line growth with an IC50 of 0.216 +/- 0.031 mu M. Apoptosis analysis indicated different contributions of early/late apoptosis/necrosis to cell death for both monomers, the combination (D + P in 1:1 mol ratio) and D-P-4. They all arrested more cells on S phase. Western Blot implied that D-P-4 regulated p53/MDM2 to a better healthy state. Moreover, it improved Bax/Bcl-2 signaling pathway to increase cancer cell apoptosis. In all cases studied, D-P-4 showed the best activity and synergistic effect. All the evidences support that D-P-4 is a better anti-cancer therapy with multi-target functions. (C) 2017 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2017.10.074
• 作为产物：
  描述：

  3,4-二羟基氧杂蒽酮 在 sodium hydroxide 作用下， 以 氯仿 、 N,N-二甲基甲酰胺 为溶剂， 反应 24.67h， 生成 3,4-dihydro-12-O-(6'-hydroxyhexyl)-2,2-dimethyl-2H,6H-pyrano[3,2-b]xanthen-6-one
  参考文献：
  名称：

  DMXAA-pyranoxanthone hybrids enhance inhibition activities against human cancer cells with multi-target functions

  摘要：

  Four 5,6-dimethylxanthone-4-acetic acid (D) and pyranoxanthone (P) hybrids (D-P-n) were design-synthesized based on multi-target-addressed strategy. D-P-4 was confirmed as the most active agent against HepG-2 cell line growth with an IC50 of 0.216 +/- 0.031 mu M. Apoptosis analysis indicated different contributions of early/late apoptosis/necrosis to cell death for both monomers, the combination (D + P in 1:1 mol ratio) and D-P-4. They all arrested more cells on S phase. Western Blot implied that D-P-4 regulated p53/MDM2 to a better healthy state. Moreover, it improved Bax/Bcl-2 signaling pathway to increase cancer cell apoptosis. In all cases studied, D-P-4 showed the best activity and synergistic effect. All the evidences support that D-P-4 is a better anti-cancer therapy with multi-target functions. (C) 2017 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2017.10.074

文献信息

• DMXAA-pyranoxanthone hybrids enhance inhibition activities against human cancer cells with multi-target functions
  作者：Jie Liu、Fan Zhou、Lei Zhang、Huailing Wang、Jianrun Zhang、Cao Zhang、Zhenlei Jiang、Yanbing Li、Zhijun Liu、Heru Chen

  DOI：10.1016/j.ejmech.2017.10.074

  日期：2018.1

  Four 5,6-dimethylxanthone-4-acetic acid (D) and pyranoxanthone (P) hybrids (D-P-n) were design-synthesized based on multi-target-addressed strategy. D-P-4 was confirmed as the most active agent against HepG-2 cell line growth with an IC50 of 0.216 +/- 0.031 mu M. Apoptosis analysis indicated different contributions of early/late apoptosis/necrosis to cell death for both monomers, the combination (D + P in 1:1 mol ratio) and D-P-4. They all arrested more cells on S phase. Western Blot implied that D-P-4 regulated p53/MDM2 to a better healthy state. Moreover, it improved Bax/Bcl-2 signaling pathway to increase cancer cell apoptosis. In all cases studied, D-P-4 showed the best activity and synergistic effect. All the evidences support that D-P-4 is a better anti-cancer therapy with multi-target functions. (C) 2017 Elsevier Masson SAS. All rights reserved.