3-(2,2-dimethylchroman-6-carboxamido)-7-(2,3,4,6-tetra-O-acetyl-β-glucopyranos-1-yl)-8-methyl-2-oxo-2H-chromen-4-yl 4-methylbenzenesulfonate | 1620838-64-3

• 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: 3-(2,2-dimethylchroman-6-carboxamido)-7-(2,3,4,6-tetra-O-acetyl-β-glucopyranos-1-yl)-8-methyl-2-oxo-2H-chromen-4-yl 4-methylbenzenesulfonate
• 英文别名: [(2R,3R,4S,5R,6S)-3,4,5-triacetyloxy-6-[3-[(2,2-dimethyl-3,4-dihydrochromene-6-carbonyl)amino]-8-methyl-4-(4-methylphenyl)sulfonyloxy-2-oxochromen-7-yl]oxyoxan-2-yl]methyl acetate
• CAS: 1620838-64-3
• 化学式: C₄₃H₄₅NO₁₇S
• 分子量: 879.893
• InChiKey: SLJJLBMYRFVVLA-NEMVALRASA-N

物化性质

• 熔点：
  143-145 °C
• 沸点：
  940.1±65.0 °C(predicted)
• 密度：
  1.44±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  62
• 可旋转键数：
  16
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  240
• 氢给体数：
  1
• 氢受体数：
  17

反应信息

• 作为反应物：
  描述：

  3-(2,2-dimethylchroman-6-carboxamido)-7-(2,3,4,6-tetra-O-acetyl-β-glucopyranos-1-yl)-8-methyl-2-oxo-2H-chromen-4-yl 4-methylbenzenesulfonate 在 氨 作用下， 以 四氢呋喃 为溶剂， 反应 24.0h， 以27%的产率得到N-(4-amino-7-(2,3,4,6-tetra-O-acetyl-β-glucopyranos-1-yl)-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
• 作为产物：
  描述：

  sodium novobiocin 在 吡啶 、 偶氮二甲酸二异丙酯 、 三苯基膦 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 反应 27.5h， 生成 3-(2,2-dimethylchroman-6-carboxamido)-7-(2,3,4,6-tetra-O-acetyl-β-glucopyranos-1-yl)-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