(1E,4E,6E)-1-(1-isopropyl-1H-imidazol-2-yl)-7-(2-methyl-4-(trifluoromethyl)thiazol-5-yl)hepta-1,4,6-trien-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,6E)-1-(1-isopropyl-1H-imidazol-2-yl)-7-(2-methyl-4-(trifluoromethyl)thiazol-5-yl)hepta-1,4,6-trien-3-one
• 英文别名: (1E,4E,6E)-7-[2-methyl-4-(trifluoromethyl)-1,3-thiazol-5-yl]-1-(1-propan-2-ylimidazol-2-yl)hepta-1,4,6-trien-3-one
• 化学式: C₁₈H₁₈F₃N₃OS
• 分子量: 381.422
• InChiKey: SDWVARPDXCXCHA-SFYXYOTASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  26
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  76
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  在 potassium carbonate 作用下， 以 乙醇 、 水 为溶剂， 反应 0.5h， 生成 (1E,4E,6E)-1-(1-isopropyl-1H-imidazol-2-yl)-7-(2-methyl-4-(trifluoromethyl)thiazol-5-yl)hepta-1,4,6-trien-3-one
  参考文献：
  名称：

  Structure-activity relationship studies of 1,7-diheteroarylhepta-1,4,6-trien-3-ones with two different terminal rings in prostate epithelial cell models

  摘要：

  To systematically investigate the structure-activity relationships of 1,7-diarylhepta-1,4,6-trien-3-ones in three human prostate cancer cell models and one human prostate non-neoplastic epithelial cell model, thirty five 1,7-diarylhepta-1,4,6-trien-3-ones with different terminal heteroaromatic rings have been designed for evaluation of their anti-proliferative potency in vitro. These target compounds have been successfully synthesized through two sequential Horner-Wadsworth-Emmons reactions starting from the appropriate aldehydes and tetraethyl (2-oxopropane-1,3-diyl)bis(phosphonate). Their anti-proliferative potency against PC-3, DU-145 and LNCaP human prostate cancer cell lines can be significantly enhanced by the manipulation of the terminal heteroaromatic rings, further demonstrating the utility of 1,7-diarylhepta-1,4,6-trien-3-one as a potential scaffold for the development of anti prostate cancer agents. The optimal analog 40 is 82-, 67-, and 39-fold more potent than curcumin toward the three prostate cancer cell lines, respectively. The experimental data also reveal that the trienones with two different terminal aromatic rings possess greater potency toward three prostate cancer cell lines, but also have greater capability of suppressing the proliferation of PWR-1E benign human prostate epithelial cells, as compared to the corresponding counterparts with two identical terminal rings and curcumin. The terminal aromatic rings also affect the cell apoptosis perturbation. (C) 2017 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2017.03.067

文献信息

• Structure-activity relationship studies of 1,7-diheteroarylhepta-1,4,6-trien-3-ones with two different terminal rings in prostate epithelial cell models
  作者：Rubing Wang、Xiaojie Zhang、Chengsheng Chen、Guanglin Chen、Cristian Sarabia、Qiang Zhang、Shilong Zheng、Guangdi Wang、Qiao-Hong Chen

  DOI：10.1016/j.ejmech.2017.03.067

  日期：2017.6

  To systematically investigate the structure-activity relationships of 1,7-diarylhepta-1,4,6-trien-3-ones in three human prostate cancer cell models and one human prostate non-neoplastic epithelial cell model, thirty five 1,7-diarylhepta-1,4,6-trien-3-ones with different terminal heteroaromatic rings have been designed for evaluation of their anti-proliferative potency in vitro. These target compounds have been successfully synthesized through two sequential Horner-Wadsworth-Emmons reactions starting from the appropriate aldehydes and tetraethyl (2-oxopropane-1,3-diyl)bis(phosphonate). Their anti-proliferative potency against PC-3, DU-145 and LNCaP human prostate cancer cell lines can be significantly enhanced by the manipulation of the terminal heteroaromatic rings, further demonstrating the utility of 1,7-diarylhepta-1,4,6-trien-3-one as a potential scaffold for the development of anti prostate cancer agents. The optimal analog 40 is 82-, 67-, and 39-fold more potent than curcumin toward the three prostate cancer cell lines, respectively. The experimental data also reveal that the trienones with two different terminal aromatic rings possess greater potency toward three prostate cancer cell lines, but also have greater capability of suppressing the proliferation of PWR-1E benign human prostate epithelial cells, as compared to the corresponding counterparts with two identical terminal rings and curcumin. The terminal aromatic rings also affect the cell apoptosis perturbation. (C) 2017 Elsevier Masson SAS. All rights reserved.