2,6-bis(3-bromo-4-methoxybenzylidene)cyclohexanone | 340988-32-1

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二芳基庚烷
• 英文名称: 2,6-bis(3-bromo-4-methoxybenzylidene)cyclohexanone
• 英文别名: 2,6-Bis[(3-bromo-4-methoxyphenyl)methylidene]cyclohexan-1-one；2,6-bis[(3-bromo-4-methoxyphenyl)methylidene]cyclohexan-1-one
• CAS: 340988-32-1
• 化学式: C₂₂H₂₀Br₂O₃
• mdl: MFCD14722764
• 分子量: 492.207
• InChiKey: MBOWWLGNTZGSQT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.4
• 重原子数：
  27
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  3-溴-4-甲氧基苯甲醛 、 环己酮 在 barium hydroxide octahydrate 作用下， 以 甲醇 为溶剂， 反应 2.0h， 以82%的产率得到2,6-bis(3-bromo-4-methoxybenzylidene)cyclohexanone
  参考文献：
  名称：

  Identification of PR-SET7 and EZH2 selective inhibitors inducing cell death in human leukemia U937 cells

  摘要：

  Chemical manipulations undertaken on some bis(bromo- and dibromo-phenol) compounds previously reported by us as wide-spectrum epigenetic inhibitors let us to identify bis (bromo- and dibromo-methoxyphenyl) derivatives highly selective for PR-SET7 and EZH2 (compounds 4, 5, 9, and 10). Western blot analyses were carried out in U937 cells to determine the effects of such compounds on the methyl marks related to the tested enzymes (H3K4me1, H3K9me2, H4H20me1, and H3K27me3). The 1,5-bis(3-bromo-4-methoxyphenyl)penta-1,4-dien-3-one 4 (EC50, vs EZH2 = 74.9 mu M), tested in U937 cells at 50 mu M, induced massive cell death and 28% of granulocytic differentiation, highlighting the potential use of EZH2 inhibitors in cancer. (C) 2012 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.biochi.2012.06.003

文献信息

• Identification of PR-SET7 and EZH2 selective inhibitors inducing cell death in human leukemia U937 cells
  作者：Sergio Valente、Ilaria Lepore、Carmela Dell'Aversana、Maria Tardugno、Sabrina Castellano、Gianluca Sbardella、Stefano Tomassi、Salvatore Di Maro、Ettore Novellino、Roberto Di Santo、Roberta Costi、Lucia Altucci、Antonello Mai

  DOI：10.1016/j.biochi.2012.06.003

  日期：2012.11

  Chemical manipulations undertaken on some bis(bromo- and dibromo-phenol) compounds previously reported by us as wide-spectrum epigenetic inhibitors let us to identify bis (bromo- and dibromo-methoxyphenyl) derivatives highly selective for PR-SET7 and EZH2 (compounds 4, 5, 9, and 10). Western blot analyses were carried out in U937 cells to determine the effects of such compounds on the methyl marks related to the tested enzymes (H3K4me1, H3K9me2, H4H20me1, and H3K27me3). The 1,5-bis(3-bromo-4-methoxyphenyl)penta-1,4-dien-3-one 4 (EC50, vs EZH2 = 74.9 mu M), tested in U937 cells at 50 mu M, induced massive cell death and 28% of granulocytic differentiation, highlighting the potential use of EZH2 inhibitors in cancer. (C) 2012 Elsevier Masson SAS. All rights reserved.