(1E,4E)-1,5-bis(2-bromo-6-fluorophenyl)penta-1,4-dien-3-one | 1600528-61-7

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: (1E,4E)-1,5-bis(2-bromo-6-fluorophenyl)penta-1,4-dien-3-one
• CAS: 1600528-61-7
• 化学式: C₁₇H₁₀Br₂F₂O
• 分子量: 428.071
• InChiKey: LUFQEAWDGKKFLA-FIFLTTCUSA-N

物化性质

• 熔点：
  161.5-163.7 °C
• 沸点：
  477.907±45.00 °C(Press: 760.00 Torr)(predicted)
• 密度：
  1.687±0.06 g/cm3(Temp: 25 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2-溴-6-氟苯甲醛 、 丙酮 在 potassium hydroxide 作用下， 以 乙醇 为溶剂， 反应 1.16h， 以71.1%的产率得到(1E,4E)-1,5-bis(2-bromo-6-fluorophenyl)penta-1,4-dien-3-one
  参考文献：
  名称：

  Synthesis of novel curcumin analogues for inhibition of 11β-hydroxysteroid dehydrogenase type 1 with anti-diabetic properties

  摘要：

  In the present study, a series of mono-carbonyl analogues of curcumin were designed and synthesized by deleting the reactive beta-diketone moiety, which is responsible for the pharmacokinetic limitation of curcumin. We demonstrated that 4 of 9 curcumin analogues were selective inhibitors of human and rodent 11 beta-HSD1. The level of this inhibitor was 4-20 times more than that of curcumin. Curcumin analogues weakly inhibited 11 beta-HSD2, and further analyses revealed that these compounds were highly selective, favoring 11 beta-HSD1. These 4 curcumin analogues are potential therapeutic agents for type-2 diabetes by targeting 11 beta-HSD1. The compound 8 displays anti-diabetic properties in diabetic mice induced by streptozocin and high-fat-diet (STZHFD). (C) 2014 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2014.03.012

文献信息

• Synthesis of novel curcumin analogues for inhibition of 11β-hydroxysteroid dehydrogenase type 1 with anti-diabetic properties
  作者：Xiaohuan Yuan、Hongzhi Li、He Bai、Zhijian Su、Qi Xiang、Chaonan Wang、Binghai Zhao、Yufei Zhang、Qihao Zhang、Yanhui Chu、Yadong Huang

  DOI：10.1016/j.ejmech.2014.03.012

  日期：2014.4

  In the present study, a series of mono-carbonyl analogues of curcumin were designed and synthesized by deleting the reactive beta-diketone moiety, which is responsible for the pharmacokinetic limitation of curcumin. We demonstrated that 4 of 9 curcumin analogues were selective inhibitors of human and rodent 11 beta-HSD1. The level of this inhibitor was 4-20 times more than that of curcumin. Curcumin analogues weakly inhibited 11 beta-HSD2, and further analyses revealed that these compounds were highly selective, favoring 11 beta-HSD1. These 4 curcumin analogues are potential therapeutic agents for type-2 diabetes by targeting 11 beta-HSD1. The compound 8 displays anti-diabetic properties in diabetic mice induced by streptozocin and high-fat-diet (STZHFD). (C) 2014 Elsevier Masson SAS. All rights reserved.