3,5-bis(3-bromo-4-hydroxybenzylidene)-1-(4-chlorobenzyl)piperidin-4-one | 1312442-63-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: 3,5-bis(3-bromo-4-hydroxybenzylidene)-1-(4-chlorobenzyl)piperidin-4-one
• 英文别名: 3,5-bis[(3-bromo-4-hydroxyphenyl)methylidene]-1-[(4-chlorophenyl)methyl]piperidin-4-one
• CAS: 1312442-63-9
• 化学式: C₂₆H₂₀Br₂ClNO₃
• 分子量: 589.711
• InChiKey: RADKNBVRRFNZJK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.83
• 重原子数：
  33.0
• 可旋转键数：
  4.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  60.77
• 氢给体数：
  2.0
• 氢受体数：
  4.0

反应信息

• 作为产物：
  描述：

  3-bromo-4-(methoxymethoxy)benzaldehyde 在 盐酸 、 barium hydroxide octahydrate 、 potassium carbonate 作用下， 以 甲醇 、 水 、 乙腈 为溶剂， 反应 6.0h， 生成 3,5-bis(3-bromo-4-hydroxybenzylidene)-1-(4-chlorobenzyl)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

文献信息

• Novel 3,5-Bis(bromohydroxybenzylidene)piperidin-4-ones as Coactivator-Associated Arginine Methyltransferase 1 Inhibitors: Enzyme Selectivity and Cellular Activity
  作者：Donghang Cheng、Sergio Valente、Sabrina Castellano、Gianluca Sbardella、Roberto Di Santo、Roberta Costi、Mark T. Bedford、Antonello Mai

  DOI：10.1021/jm200453n

  日期：2011.7.14

  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.