N-(6-bromo-4,7-dimethoxy-8-methyl-2-oxo-2H-chromen-3-yl)-2,2-dimethylchroman-6-carboxamide | 1620841-73-7

• 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: N-(6-bromo-4,7-dimethoxy-8-methyl-2-oxo-2H-chromen-3-yl)-2,2-dimethylchroman-6-carboxamide
• 英文别名: N-(6-bromo-4,7-dimethoxy-8-methyl-2-oxochromen-3-yl)-2,2-dimethyl-3,4-dihydrochromene-6-carboxamide
• CAS: 1620841-73-7
• 化学式: C₂₄H₂₄BrNO₆
• 分子量: 502.362
• InChiKey: DWGWQVPUVGNJQN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  32
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  83.1
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  N-(6-bromo-4,7-dimethoxy-8-methyl-2-oxo-2H-chromen-3-yl)-2,2-dimethylchroman-6-carboxamide 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 三乙胺 、 三苯基膦 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 12.58h， 生成 3-(2,2-dimethylchroman-6-carboxamido)-7-methoxy-8-methyl-2-oxo-6-((3,4,5-trimethoxyphenyl)ethynyl)-2H-chromen-4-yl 4-methylbenzenesulfonate
  参考文献：
  名称：

  Synthesis and antiproliferative activity of novobiocin analogues as potential hsp90 inhibitors

  摘要：

  A series of substituted coumarins1-10 was designed and synthesized as a novel class of 4TCNA analogues. Compound 2a showed excellent antiproliferative activity with mean GI50 values at a micromolar level in a diverse set of human cancer cells (GI50 = 2-30 μM) and induced a high apoptosis level in MCF-7 breast cancer cell line. The molecular signature of hsp90 inhibition was assessed by depletion of the Erα hsp90 client protein.

  DOI：

  10.1016/j.ejmech.2014.06.067
• 作为产物：
  描述：

  sodium novobiocin 在 N-methylpyrrolidin-2-one hydrotribromide 、 potassium carbonate 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 27.0h， 生成 N-(6-bromo-4,7-dimethoxy-8-methyl-2-oxo-2H-chromen-3-yl)-2,2-dimethylchroman-6-carboxamide
  参考文献：
  名称：

  Synthesis and antiproliferative activity of novobiocin analogues as potential hsp90 inhibitors

  摘要：

  A series of substituted coumarins1-10 was designed and synthesized as a novel class of 4TCNA analogues. Compound 2a showed excellent antiproliferative activity with mean GI50 values at a micromolar level in a diverse set of human cancer cells (GI50 = 2-30 μM) and induced a high apoptosis level in MCF-7 breast cancer cell line. The molecular signature of hsp90 inhibition was assessed by depletion of the Erα hsp90 client protein.

  DOI：

  10.1016/j.ejmech.2014.06.067

文献信息

• Synthesis and antiproliferative activity of novobiocin analogues as potential hsp90 inhibitors
  作者：Davide Audisio、Délphine Methy-Gonnot、Christine Radanyi、Jack-Michel Renoir、Stéphanie Denis、Félix Sauvage、Juliette Vergnaud-Gauduchon、Jean-Daniel Brion、Samir Messaoudi、Mouad Alami

  DOI：10.1016/j.ejmech.2014.06.067

  日期：2014.8

  A series of substituted coumarins1-10 was designed and synthesized as a novel class of 4TCNA analogues. Compound 2a showed excellent antiproliferative activity with mean GI50 values at a micromolar level in a diverse set of human cancer cells (GI50 = 2-30 μM) and induced a high apoptosis level in MCF-7 breast cancer cell line. The molecular signature of hsp90 inhibition was assessed by depletion of the Erα hsp90 client protein.