N,N'-{[(1E,3E)-5-methyl-2-oxocyclohexane-1,3-diylidene]bis[methylylidene-3,1-phenylene]}bis(2-bromoacrylamide) | 1228557-76-3

• 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: N,N'-{[(1E,3E)-5-methyl-2-oxocyclohexane-1,3-diylidene]bis[methylylidene-3,1-phenylene]}bis(2-bromoacrylamide)
• 英文别名: 2-bromo-N-[3-[(E)-[(3E)-3-[[3-(2-bromoprop-2-enoylamino)phenyl]methylidene]-5-methyl-2-oxocyclohexylidene]methyl]phenyl]prop-2-enamide
• CAS: 1228557-76-3
• 化学式: C₂₇H₂₄Br₂N₂O₃
• 分子量: 584.307
• InChiKey: ZLZIYDMSOSZJAP-ADYPVIEZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.6
• 重原子数：
  34
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  75.3
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2-溴丙烯酸 、 (2E,6E)-2,6-bis[(3-aminophenyl)methylidene]-4-methylcyclohexan-1-one 在 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以54%的产率得到N,N'-{[(1E,3E)-5-methyl-2-oxocyclohexane-1,3-diylidene]bis[methylylidene-3,1-phenylene]}bis(2-bromoacrylamide)
  参考文献：
  名称：

  Symmetrical α-bromoacryloylamido diaryldienone derivatives as a novel series of antiproliferative agents. Design, synthesis and biological evaluation

  摘要：

  In a continuing study of hybrid compounds containing the alpha-bromoacryloyl moiety as potential anticancer drugs, we synthesized a novel series of hybrids 4a-h, in which this moiety was linked to a 1,5-diaryl-1,4-pentadien-3-one system. Many of the conjugates prepared (4b, 4c, 4e and 4g) demonstrated pronounced, submicromolar antiproliferative activity against four cancer cell lines. Moreover, compound 4b induced apoptosis through the mitochondrial pathway and activated caspase-3 in a concentration-dependent manner. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.03.075