N-(6-ethynyl-4-hydroxy-7-methoxy-8-methyl-2-oxo-2H-chromen-3-yl)-2,2-dimethylchroman-6-carboxamide | 1620841-67-9

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 香豆素及其衍生物
• 英文名称: N-(6-ethynyl-4-hydroxy-7-methoxy-8-methyl-2-oxo-2H-chromen-3-yl)-2,2-dimethylchroman-6-carboxamide
• CAS: 1620841-67-9
• 化学式: C₂₅H₂₃NO₆
• 分子量: 433.461
• InChiKey: ALYGETOZLIBJRK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.15
• 重原子数：
  32.0
• 可旋转键数：
  3.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  98.0
• 氢给体数：
  2.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  N-(6-ethynyl-4-hydroxy-7-methoxy-8-methyl-2-oxo-2H-chromen-3-yl)-2,2-dimethylchroman-6-carboxamide 、 对甲苯磺酰氯 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 12.08h， 以39%的产率得到3-(2,2-dimethylchroman-6-carboxamido)-6-ethynyl-7-methoxy-8-methyl-2-oxo-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 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 N-methylpyrrolidin-2-one hydrotribromide 、 potassium carbonate 、 三乙胺 、 三苯基膦 作用下， 以 甲醇 、 乙醇 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 29.5h， 生成 N-(6-ethynyl-4-hydroxy-7-methoxy-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