1,3,6-tris(3-methylbut-2-enyloxy)-9H-xanthen-9-one | 1381788-12-0

• 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: 1,3,6-tris(3-methylbut-2-enyloxy)-9H-xanthen-9-one
• 英文别名: 1,3,6-Tris(3-methylbut-2-enoxy)xanthen-9-one
• CAS: 1381788-12-0
• 化学式: C₂₈H₃₂O₅
• 分子量: 448.559
• InChiKey: ITYKFARKGGXMCA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.4
• 重原子数：
  33
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  54
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  2,4-二羟基苯甲酸 在 Eaton′s Reagent 、 potassium iodide 、 potassium hydroxide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 25.17h， 生成 1,6-dihydroxy-3-(3-methylbut-2-enyloxy)-9H-xanthen-9-one 、 1,3,6-tris(3-methylbut-2-enyloxy)-9H-xanthen-9-one 、 1-hydroxy-2-(3-methylbut-2-enyl)-3,6-bis(3-methylbut-2-enyloxy)-9H-xanthen-9-one 、 1-hydroxy-3,6-bis(3-methylbut-2-enyloxy)-9H-xanthen-9-one
  参考文献：
  名称：

  Design and synthesis of gambogic acid analogs as potent cytotoxic and anti-inflammatory agents

  摘要：

  Prenyl-and pyrano-xanthones derived from 1,3,6-trihydroxy-9H-xanthen-9-one, a basic backbone of gambogic acid (GA), were synthesized and evaluated for in vitro cytotoxic effects against four human cancer cell lines (KB, KBvin, A549, and DU-145) and anti-inflammatory activity toward superoxide anion generation and elastase release by human neutrophils in response to fMLP/CB. Among them, prenylxanthones 7-13 were generally less active than pyranoxanthones 14-21 in both anticancer and anti-inflammatory assays. Furthermore, two angular 3,3-dimethypyranoxanthones (16 and 20) showed the greatest and selective activity against the KBvin multidrug resistant (MDR) cell line with IC50 values of 0.9 and 0.8 mu g/mL, respectively. An angular 3-methyl-3-prenylpyranoxanthone (17) selectively inhibited elastase release with 200 times more potency than phenylmethylsulfonyl fluoride (PMSF), the positive control. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.04.084

文献信息

• Design and synthesis of gambogic acid analogs as potent cytotoxic and anti-inflammatory agents
  作者：Chiao-Ting Yen、Kyoko Nakagawa-Goto、Tsong-Long Hwang、Susan L. Morris-Natschke、Kenneth F. Bastow、Yang-Chang Wu、Kuo-Hsiung Lee

  DOI：10.1016/j.bmcl.2012.04.084

  日期：2012.6

  Prenyl-and pyrano-xanthones derived from 1,3,6-trihydroxy-9H-xanthen-9-one, a basic backbone of gambogic acid (GA), were synthesized and evaluated for in vitro cytotoxic effects against four human cancer cell lines (KB, KBvin, A549, and DU-145) and anti-inflammatory activity toward superoxide anion generation and elastase release by human neutrophils in response to fMLP/CB. Among them, prenylxanthones 7-13 were generally less active than pyranoxanthones 14-21 in both anticancer and anti-inflammatory assays. Furthermore, two angular 3,3-dimethypyranoxanthones (16 and 20) showed the greatest and selective activity against the KBvin multidrug resistant (MDR) cell line with IC50 values of 0.9 and 0.8 mu g/mL, respectively. An angular 3-methyl-3-prenylpyranoxanthone (17) selectively inhibited elastase release with 200 times more potency than phenylmethylsulfonyl fluoride (PMSF), the positive control. (C) 2012 Elsevier Ltd. All rights reserved.