9-Chloro-5-methoxy-2,2-dimethyl-3,4-dihydropyrano[2,3-b]xanthen-11-one | 1435269-82-1

• 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-Chloro-5-methoxy-2,2-dimethyl-3,4-dihydropyrano[2,3-b]xanthen-11-one
• 英文别名: 9-chloro-5-methoxy-2,2-dimethyl-3,4-dihydropyrano[2,3-b]xanthen-11-one
• CAS: 1435269-82-1
• 化学式: C₁₉H₁₇ClO₄
• 分子量: 344.795
• InChiKey: CUWWRBVMFNSMBY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  24
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  5-羟基-2,2-二甲基-2H-色烯-6-甲醛 在 potassium hydrogensulfate 、 正丁基锂 、 四甲基乙二胺 、 双氧水 、 potassium carbonate 作用下， 以 四氢呋喃 、 甲醇 、 水 、 丙酮 为溶剂， 反应 56.0h， 生成 9-Chloro-5-methoxy-2,2-dimethyl-3,4-dihydropyrano[2,3-b]xanthen-11-one
  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.