5,9-dihydroxy-2,2-dimethyl-2H,6H-pyrano<3,2-b>xanthen-6-one | 94141-73-8

• 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: 5,9-dihydroxy-2,2-dimethyl-2H,6H-pyrano<3,2-b>xanthen-6-one
• 英文别名: 5,9-dihydroxy-2,2-dimethylpyrano[3,2-b]xanthen-6(2H)-one；5,9-Dihydroxy-2,2-dimethylpyrano[3,2-b]xanthen-6-one
• CAS: 94141-73-8
• 化学式: C₁₈H₁₄O₅
• 分子量: 310.306
• InChiKey: XCYFDMOOTOIGNY-UHFFFAOYSA-N

物化性质

• 沸点：
  540.2±50.0 °C(Predicted)
• 密度：
  1.410±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  23
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  76
• 氢给体数：
  2
• 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 、 calcium hydroxide 作用下， 以 甲醇 为溶剂， 反应 37.0h， 生成 5,9-dihydroxy-2,2-dimethyl-2H,6H-pyrano<3,2-b>xanthen-6-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

• Synthesis of some 1,3,6-trioxygenated isopentenylated xanthones
  作者：V.K. Ahluwalia、A.K. Tehim

  DOI：10.1016/0040-4020(84)85015-2

  日期：1984.1

  3-methylbut-2enylated xanthones, is described. Synthesis of 1,3,6-trihydroxy-2,4-bis(3-methylbut-2-enyl)-9H- xanthen-9-one, designed as garcinone A and reported as a natural product from the fruit-hulls of Garcinia mangostana (Guttiferae), has also been achieved. However synthetic xanthone is found to be different from natural garcinone A, therefore its constitution needs reinvestigation.

  在甲醇甲醇钠的存在下，1,3-二羟基-6-甲氧基和1,3,6-三羟基黄酮与1-溴3-甲基丁-2-烯反应，得到相应的3-甲基丁-2-烯基化的氧杂蒽，描述。1,3,6-三羟基-2,4-双（3-甲基丁-2-烯基）-9H-黄嘌呤-9-的合成，设计为藤黄酮A，据报道是藤黄果皮的天然产物柿（藤黄科），也已经实现。然而，发现合成的an吨酮与天然的藤黄酮A不同，因此其构成需要重新研究。
• 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.