3,3-dimethyl-6-hydroxy-2-nitro-3H,7H-pyrano[2,3-c]xanthen-7-one | 935872-51-8

• 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: 3,3-dimethyl-6-hydroxy-2-nitro-3H,7H-pyrano[2,3-c]xanthen-7-one
• 英文别名: 6-Hydroxy-3,3-dimethyl-2-nitropyrano[2,3-c]xanthen-7-one
• CAS: 935872-51-8
• 化学式: C₁₈H₁₃NO₆
• 分子量: 339.304
• InChiKey: VBPYWAFZHBLJLQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  25
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  102
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  3,3-dimethyl-6-hydroxy-2-nitro-3H,7H-pyrano[2,3-c]xanthen-7-one 在 sodium tetrahydroborate 、 镍 、 三乙胺 、 肼 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 0.25h， 生成 tert-butyl N-[1,2-dihydro-6-(2-diethylaminoethylamino)-3,3-dimethyl-7-oxo-3H,7H-pyrano[2,3-c]xanthen-2-yl]carbamate
  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：

  3,3-dimethyl-6-(4-methylphenylsulfonyloxy)-3H,7H-pyrano[2,3-c]xanthen-7-one 在 sodium hydroxide 、 硝酸 、 溶剂黄146 作用下， 以 乙醇 、 水 为溶剂， 反应 1.0h， 生成 3,3-dimethyl-6-hydroxy-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

文献信息

• 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
  作者：George Kolokythas、Ioannis K. Kostakis、Nicole Pouli、Panagiotis Marakos、Olga Ch. Kousidou、George N. Tzanakakis、Nikos K. Karamanos

  DOI：10.1016/j.ejmech.2006.10.018

  日期：2007.3

  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.