9,12-Dihydroxy-2,2-dimethyl-3,4-dihydropyrano[3,2-b]xanthen-6-one | 1435267-34-7

• 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: 9,12-Dihydroxy-2,2-dimethyl-3,4-dihydropyrano[3,2-b]xanthen-6-one
• 英文别名: 9,12-dihydroxy-2,2-dimethyl-3,4-dihydropyrano[3,2-b]xanthen-6-one
• CAS: 1435267-34-7
• 化学式: C₁₈H₁₆O₅
• 分子量: 312.322
• InChiKey: BEYLUVYOQJUNBE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  23
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.28
• 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：

  2,4-二苄氧基苯甲醛 在 三乙基硅烷 、 正丁基锂 、 palladium 10% on activated carbon 、 2-碘酰基苯甲酸 作用下， 以 四氢呋喃 、 甲醇 、 二甲基亚砜 为溶剂， 反应 24.75h， 生成 pyranoxanthone 、 9,12-Dihydroxy-2,2-dimethyl-3,4-dihydropyrano[3,2-b]xanthen-6-one 、 (2,4-dihydroxyphenyl)(8-hydroxy-7-methoxy-2,2-dimethyl-3,4-dihydrobenzopyran-6-yl)methanone
  参考文献：
  名称：

  Multidimensional optimization of promising antitumor xanthone derivatives

  摘要：

  A promising antitumor xanthone derivative was optimized following a multidimensional approach that involved the synthesis of 17 analogues, the study of their lipophilicity and solubility, and the evaluation of their growth inhibitory activity on four human tumor cell lines. A new synthetic route for the hit xanthone derivative was also developed and applied for the synthesis of its analogues. Among the used cell lines, the HL-60 showed to be in general more sensitive to the compounds tested, with the most potent compound having a GI(50) of 5.1 mu M, lower than the hit compound. Lipophilicity was evaluated by the partition coefficient (K-p) of a solute between buffer and two membrane models, namely liposomes and micelles. The compounds showed a log K-p between 3 and 5 and the two membrane models showed a good correlation (r(2) = 0.916) between each other. Studies concerning relationship between solubility and structure were developed for the hit compound and 5 of its analogues. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2013.03.079

文献信息

• Multidimensional optimization of promising antitumor xanthone derivatives
  作者：Carlos M.G. Azevedo、Carlos M.M. Afonso、Diana Sousa、Raquel T. Lima、M. Helena Vasconcelos、Madalena Pedro、João Barbosa、Arlene G. Corrêa、Salette Reis、Madalena M.M. Pinto

  DOI：10.1016/j.bmc.2013.03.079

  日期：2013.6

  A promising antitumor xanthone derivative was optimized following a multidimensional approach that involved the synthesis of 17 analogues, the study of their lipophilicity and solubility, and the evaluation of their growth inhibitory activity on four human tumor cell lines. A new synthetic route for the hit xanthone derivative was also developed and applied for the synthesis of its analogues. Among the used cell lines, the HL-60 showed to be in general more sensitive to the compounds tested, with the most potent compound having a GI(50) of 5.1 mu M, lower than the hit compound. Lipophilicity was evaluated by the partition coefficient (K-p) of a solute between buffer and two membrane models, namely liposomes and micelles. The compounds showed a log K-p between 3 and 5 and the two membrane models showed a good correlation (r(2) = 0.916) between each other. Studies concerning relationship between solubility and structure were developed for the hit compound and 5 of its analogues. (C) 2013 Elsevier Ltd. All rights reserved.