3-(1,1-dimethylprop-2-ynyloxy)-1-(4-methylphenylsulfonyloxy)-9H-xanthen-9-one | 935872-25-6

• 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: 3-(1,1-dimethylprop-2-ynyloxy)-1-(4-methylphenylsulfonyloxy)-9H-xanthen-9-one
• 英文别名: [3-(2-Methylbut-3-yn-2-yloxy)-9-oxoxanthen-1-yl] 4-methylbenzenesulfonate
• CAS: 935872-25-6
• 化学式: C₂₅H₂₀O₆S
• 分子量: 448.496
• InChiKey: ABNBJGJRLPOODR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  32
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.16
• 拓扑面积：
  87.3
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  3-(1,1-dimethylprop-2-ynyloxy)-1-(4-methylphenylsulfonyloxy)-9H-xanthen-9-one 在 sodium hydroxide 、 硝酸 、 sodium hydride 、 溶剂黄146 作用下， 以 四氢呋喃 、 乙醇 、 正己烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 6.0h， 生成 3,3-dimethyl-6-methoxy-2-nitro-3H,7H-pyrano[2,3-c]xanthen-7-one
  参考文献：
  名称：

  Design and synthesis of new pyranoxanthenones bearing a nitro group or an aminosubstituted side chain on the pyran ring. Evaluation of their growth inhibitory activity in breast cancer cells

  摘要：

  Some new 2,6-disubstituted pyrano- and 1,2-dihydropyrano[2,3-c]xanthen-7-ones have been synthesized and their antiproliferative activity has been evaluated against MDA-MB-231 breast cancer cells. The antiproliferative activity evaluation of the compounds provided evidence that a dimethylamino substituted side chain and the presence of 1,2 double bond play a key role in cell growth inhibition. Among the tested derivatives the 6-dimethylaminoethylamino-2-nitropyranoxanthenone analogue possessed a significant inhibitory effect in a wide range of concentrations. (c) 2006 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2006.10.018
• 作为产物：
  描述：

  1-hydroxy-3-(1,1-dimethyl-2-propynoxy)-9H-xanthen-9-one 、 对甲苯磺酰氯 在 potassium carbonate 作用下， 以 丙酮 为溶剂， 反应 1.5h， 以87%的产率得到3-(1,1-dimethylprop-2-ynyloxy)-1-(4-methylphenylsulfonyloxy)-9H-xanthen-9-one
  参考文献：
  名称：

  Design and synthesis of new pyranoxanthenones bearing a nitro group or an aminosubstituted side chain on the pyran ring. Evaluation of their growth inhibitory activity in breast cancer cells

  摘要：

  Some new 2,6-disubstituted pyrano- and 1,2-dihydropyrano[2,3-c]xanthen-7-ones have been synthesized and their antiproliferative activity has been evaluated against MDA-MB-231 breast cancer cells. The antiproliferative activity evaluation of the compounds provided evidence that a dimethylamino substituted side chain and the presence of 1,2 double bond play a key role in cell growth inhibition. Among the tested derivatives the 6-dimethylaminoethylamino-2-nitropyranoxanthenone analogue possessed a significant inhibitory effect in a wide range of concentrations. (c) 2006 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2006.10.018