(5,6-dimethoxy-2,2-dimethyl-2H-benzopyran-7-yl)(2-hydroxy-5-methoxyphenyl)methanone | 1435268-74-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (5,6-dimethoxy-2,2-dimethyl-2H-benzopyran-7-yl)(2-hydroxy-5-methoxyphenyl)methanone
• CAS: 1435268-74-8
• 化学式: C₂₁H₂₂O₆
• 分子量: 370.402
• InChiKey: COOAYZVIAXYTFU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.83
• 重原子数：
  27.0
• 可旋转键数：
  5.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  74.22
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为产物：
  描述：

  2,4-二羟基苯甲醛 在 potassium hydrogensulfate 、 正丁基锂 、 四甲基乙二胺 、 双氧水 、 potassium carbonate 、 calcium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 水 、 丙酮 为溶剂， 反应 104.0h， 生成 (5,6-dimethoxy-2,2-dimethyl-2H-benzopyran-7-yl)(2-hydroxy-5-methoxyphenyl)methanone 、 (5,6-dimethoxy-2,2-dimethyl-2H-benzopyran-8-yl)(2-hydroxy-5-methoxyphenyl)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