6-bromo-7,8-dimethoxy-2,2-dimethyl-3,4-dihydrobenzopyran | 1435265-70-5

• 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: 6-bromo-7,8-dimethoxy-2,2-dimethyl-3,4-dihydrobenzopyran
• CAS: 1435265-70-5
• 化学式: C₁₃H₁₇BrO₃
• 分子量: 301.18
• InChiKey: LTWRAOFLXCMBMG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.57
• 重原子数：
  17.0
• 可旋转键数：
  2.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  27.69
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  6-bromo-7,8-dimethoxy-2,2-dimethyl-3,4-dihydrobenzopyran 在 三乙基硅烷 、 正丁基锂 、 palladium 10% on activated carbon 、 potassium carbonate 、 2-碘酰基苯甲酸 作用下， 以 四氢呋喃 、 甲醇 、 二甲基亚砜 、 N,N-二甲基甲酰胺 为溶剂， 反应 12.75h， 生成 8,9,12-trimethoxy-2,2-dimethyl-3,4-dihydropyrano[3,2-b]xanthen-6(2H)-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
• 作为产物：
  描述：

  2,3-dimethoxy-1-((2-methylbut-3-yn-2-yl)oxy)benzene 在 三乙基硅烷 、 N-溴代丁二酰亚胺(NBS) 、 palladium 10% on activated carbon 、 ammonium acetate 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 4.58h， 生成 6-bromo-7,8-dimethoxy-2,2-dimethyl-3,4-dihydrobenzopyran
  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