3,5-bis[3-bromo-4-(methoxymethoxy)benzylidene]-1-(2-oxo-2-phenylethyl)piperidin-4-one | 1312442-57-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3,5-bis[3-bromo-4-(methoxymethoxy)benzylidene]-1-(2-oxo-2-phenylethyl)piperidin-4-one
• 英文别名: 3,5-bis[[3-bromo-4-(methoxymethoxy)phenyl]methylidene]-1-phenacylpiperidin-4-one
• CAS: 1312442-57-1
• 化学式: C₃₁H₂₉Br₂NO₆
• 分子量: 671.382
• InChiKey: PFFWLCBTIVYAJC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.41
• 重原子数：
  40.0
• 可旋转键数：
  11.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  74.3
• 氢给体数：
  0.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  3,5-bis[3-bromo-4-(methoxymethoxy)benzylidene]-1-(2-oxo-2-phenylethyl)piperidin-4-one 在 盐酸 作用下， 以 甲醇 、 水 为溶剂， 反应 3.0h， 以74%的产率得到3,5-bis(3-bromo-4-hydroxybenzylidene)-1-(2-oxo-2-phenylethyl)piperidin-4-one
  参考文献：
  名称：

  Novel 3,5-Bis(bromohydroxybenzylidene)piperidin-4-ones as Coactivator-Associated Arginine Methyltransferase 1 Inhibitors: Enzyme Selectivity and Cellular Activity

  摘要：

  Coactivator-associated arginine methyltransferase 1 (CARM1) represents a valuable target for hormone-dependent tumors such as prostate and breast cancers. Here we report the enzyme and cellular characterization of the 1-benzyl-3,5-bis(3-bromo-4-hydroxybenzylidene)piperidin-4-one (7g) and its analogues 8a-1. Among them, 7g, 8e, and 8a-1 displayed high and selective CARM1 inhibition, with lower or no activity against a panel of different PRMTs or HKMTs. In human LNCaP cells, 7g showed a significant dose-dependent reduction of the PSA promoter activity.

  DOI：

  10.1021/jm200453n
• 作为产物：
  描述：

  4-哌啶酮 在 barium hydroxide octahydrate 、 potassium carbonate 作用下， 以 甲醇 、 乙腈 为溶剂， 反应 3.0h， 生成 3,5-bis[3-bromo-4-(methoxymethoxy)benzylidene]-1-(2-oxo-2-phenylethyl)piperidin-4-one
  参考文献：
  名称：

  Novel 3,5-Bis(bromohydroxybenzylidene)piperidin-4-ones as Coactivator-Associated Arginine Methyltransferase 1 Inhibitors: Enzyme Selectivity and Cellular Activity

  摘要：

  Coactivator-associated arginine methyltransferase 1 (CARM1) represents a valuable target for hormone-dependent tumors such as prostate and breast cancers. Here we report the enzyme and cellular characterization of the 1-benzyl-3,5-bis(3-bromo-4-hydroxybenzylidene)piperidin-4-one (7g) and its analogues 8a-1. Among them, 7g, 8e, and 8a-1 displayed high and selective CARM1 inhibition, with lower or no activity against a panel of different PRMTs or HKMTs. In human LNCaP cells, 7g showed a significant dose-dependent reduction of the PSA promoter activity.

  DOI：

  10.1021/jm200453n