3-bromo-7-((1-methylpiperidin-4-yl)oxy)-2H-chromen-2-one | 1361198-91-5

• 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-bromo-7-((1-methylpiperidin-4-yl)oxy)-2H-chromen-2-one
• CAS: 1361198-91-5
• 化学式: C₁₅H₁₆BrNO₃
• 分子量: 338.201
• InChiKey: DKTRTKLDHMPBON-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.03
• 重原子数：
  20.0
• 可旋转键数：
  2.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  42.68
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  3-bromo-7-((1-methylpiperidin-4-yl)oxy)-2H-chromen-2-one 、 2-联苯硼酸 在 1,1'-双(二苯膦基)二茂铁二氯化钯(II)二氯甲烷复合物 、 potassium carbonate 作用下， 以 1,4-二氧六环 为溶剂， 反应 12.0h， 以64%的产率得到3-([1,1'-biphenyl]-2-yl)-7-((1-methylpiperidin-4-yl)oxy)-2H-chromen-2-one
  参考文献：
  名称：

  3-Arylcoumarin Derivatives Manifest Anti-proliferative Activity through Hsp90 Inhibition

  摘要：

  The potential therapeutic benefits associated with Hsp90 modulation for the treatment of cancer and neurodegenerative diseases highlight the importance of identifying novel Hsp90 scaffolds. KU-398, a novobiocin analogue, and silybin were recently identified as new Hsp90 inhibitors. Consequently, a library of 3-arylcoumarin derivatives that incorporated the structural features of KU-398 and silybin was designed, synthesized, and evaluated against two breast cancer cell lines. Western blot analysis confirmed that the resulting 3-arylcoumarin hybrids target the Hsp90 protein folding machinery.

  DOI：

  10.1021/ml300018e
• 作为产物：
  描述：

  7-甲氧基香豆素 在 N-溴代丁二酰亚胺(NBS) 、 偶氮二甲酸二异丙酯 、 sodium acetate 、 三溴化硼 、 三苯基膦 作用下， 以 四氢呋喃 、 二氯甲烷 、 乙腈 为溶剂， 反应 14.0h， 生成 3-bromo-7-((1-methylpiperidin-4-yl)oxy)-2H-chromen-2-one
  参考文献：
  名称：

  3-Arylcoumarin Derivatives Manifest Anti-proliferative Activity through Hsp90 Inhibition

  摘要：

  The potential therapeutic benefits associated with Hsp90 modulation for the treatment of cancer and neurodegenerative diseases highlight the importance of identifying novel Hsp90 scaffolds. KU-398, a novobiocin analogue, and silybin were recently identified as new Hsp90 inhibitors. Consequently, a library of 3-arylcoumarin derivatives that incorporated the structural features of KU-398 and silybin was designed, synthesized, and evaluated against two breast cancer cell lines. Western blot analysis confirmed that the resulting 3-arylcoumarin hybrids target the Hsp90 protein folding machinery.

  DOI：

  10.1021/ml300018e