(1E,4E)-1,5-bis(1-butyl-1H-imidazol-2-yl)penta-1,4-dien-3-one

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: (1E,4E)-1,5-bis(1-butyl-1H-imidazol-2-yl)penta-1,4-dien-3-one
• 英文别名: (1E,4E)-1,5-bis(1-butylimidazol-2-yl)penta-1,4-dien-3-one
• 化学式: C₁₉H₂₆N₄O
• 分子量: 326.442
• InChiKey: TXQWFPURZWNAMG-FIFLTTCUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  24
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.42
• 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：

  四乙基(2-氧代-1,3-丙烷二基)二(膦酸酯) 、 1-丁基咪唑-2-甲醛 在 potassium carbonate 作用下， 以 乙醇 、 水 为溶剂， 以95%的产率得到(1E,4E)-1,5-bis(1-butyl-1H-imidazol-2-yl)penta-1,4-dien-3-one
  参考文献：
  名称：

  Structure–Activity Relationship and Pharmacokinetic Studies of 1,5-Diheteroarylpenta-1,4-dien-3-ones: A Class of Promising Curcumin-Based Anticancer Agents

  摘要：

  Forty-three 1,5-diheteroaryl-1,4-pentadien-3-ones were designed as potential curcumin mimics, structurally featuring a central five-carbon dienone linker and two identical nitrogen-containing aromatic rings. They were synthesized using a Horner-Wadsworth-Emmons reaction as the critical step and evaluated for their cytotoxicity and antiproliferative activities toward both androgen-insensitive and androgen-sensitive prostate cancer cell lines and an aggressive cervical cancer cell line. Most of the synthesized compounds showed distinctly better in vitro potency than curcumin in the four cancer cell lines. The structure-activity data acquired from the study validated (1E,4E)-1,5-dihereroaryl-1,4-pentadien-3-ones as an excellent scaffold for in-depth development for clinical treatment of prostate and cervical cancers. 1-Alkyl-1H-imidazol-2-yl, ortho pyridyl, 1-alkyl-1H-benzo[d]imidazole-2-yl, 4-bromo-1-methyl-1H-pyrazol-3-yl, thiazol-2-yl, and 2-methyl-4-(trifluoromethyl)thiazol-5-yl were identified as optimal heteroaromatic rings for the promising in vitro potency. (1E,4E)-1,5-Bis(2-methyl-4-(trifluoromethyl)thiazol-5-yl)penta-1,4-dien-3-one, featuring thiazole rings and trifluoromethyl groups, was established as the optimal lead compound because of its good in vitro potency and attractive in vivo pharmacokinetic profiles.

  DOI：

  10.1021/acs.jmedchem.5b00470