3,5-bis(3-bromo-4-(methoxymethoxy)benzylidene)piperidin-4-one | 1312442-41-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 3,5-bis(3-bromo-4-(methoxymethoxy)benzylidene)piperidin-4-one
• 英文别名: 3,5-bis[[3-bromo-4-(methoxymethoxy)phenyl]methylidene]piperidin-4-one
• CAS: 1312442-41-3
• 化学式: C₂₃H₂₃Br₂NO₅
• 分子量: 553.247
• InChiKey: VXXYZJGKGNUGFW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.82
• 重原子数：
  31.0
• 可旋转键数：
  8.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  66.02
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  3,5-bis(3-bromo-4-(methoxymethoxy)benzylidene)piperidin-4-one 、 2-氯苄溴 在 盐酸 、 potassium carbonate 作用下， 以 甲醇 、 水 、 乙腈 为溶剂， 反应 4.0h， 生成 3,5-bis(3-bromo-4-hydroxybenzylidene)-1-(2-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
• 作为产物：
  描述：

  4-哌啶酮 、 3-bromo-4-(methoxymethoxy)benzaldehyde 在 barium hydroxide octahydrate 作用下， 以 甲醇 为溶剂， 反应 2.0h， 以77%的产率得到3,5-bis(3-bromo-4-(methoxymethoxy)benzylidene)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