(2E,6E)-2,6-bis((1-(sec-butyl)-1H-imidazol-2-yl)methylene)cyclohexanone | 1578301-15-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: (2E,6E)-2,6-bis((1-(sec-butyl)-1H-imidazol-2-yl)methylene)cyclohexanone
• 英文别名: (2E,6E)-2,6-bis[(1-butan-2-ylimidazol-2-yl)methylidene]cyclohexan-1-one
• CAS: 1578301-15-1
• 化学式: C₂₂H₃₀N₄O
• 分子量: 366.506
• InChiKey: ZHMBDSATUDSMDI-JSAVKQRWSA-N

物化性质

• 沸点：
  559.8±60.0 °C(predicted)
• 密度：
  1.12±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  27
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  52.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  1-仲-丁基-1H-咪唑-2-甲醛 、 环己酮 在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 18.0h， 以72%的产率得到(2E,6E)-2,6-bis((1-(sec-butyl)-1H-imidazol-2-yl)methylene)cyclohexanone
  参考文献：
  名称：

  Design, synthesis, and evaluation of novel heteroaromatic analogs of curcumin as anti-cancer agents

  摘要：

  To improve the potential of curcumin to treat advanced hormone-refractory prostate cancer, three series (A-C) of heteroaromatic analogs (thirty two compounds) with different monoketone linkers have been synthesized and evaluated for cytotoxicity against two human androgen-independent prostate cancer cell lines (PC-3 and DU-145). Among them, thirty analogs are more potent than curcumin against PC-3 cells, and twenty one analogs are more cytotoxic towards DU-145 cells relative to curcumin. The most potent compounds (44, 45, 51, and 52) also showed impressive cytotoxicity against three other metastatic cancer cell lines (MDA-MB-231, HeLa, and A549), with IC50 values ranging from 50 nM to 390 nM. All four most potent analogs exhibited no apparent cytotoxicity towards the MCF-10A normal mammary epithelial cells. Taken together, selective enhancement of cell death in prostate cancer cell lines and other aggressive cancer cell lines suggests that nitrogen-containing heteroaromatic rings are promising bio-isosteres of the substituted phenyl ring in curcumin. Published by Elsevier Masson SAS.

  DOI：

  10.1016/j.ejmech.2014.01.041