(3E,5E)-3,5-bis(2-bromo-6-fluorobenzylidene)piperidin-4-one | 1431524-75-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: (3E,5E)-3,5-bis(2-bromo-6-fluorobenzylidene)piperidin-4-one
• 英文别名: (3E,5E)-3,5-bis[(2-bromo-6-fluorophenyl)methylidene]piperidin-4-one
• CAS: 1431524-75-2
• 化学式: C₁₉H₁₃Br₂F₂NO
• 分子量: 469.123
• InChiKey: SASVAFFANGXIPJ-MKICQXMISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  25
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  4-哌啶酮 、 2-溴-6-氟苯甲醛 在 potassium hydroxide 作用下， 以 乙醇 为溶剂， 反应 1.16h， 以64.8%的产率得到(3E,5E)-3,5-bis(2-bromo-6-fluorobenzylidene)piperidin-4-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.