(2E,5E)-2,5-bis(2-fluoro-6-(trifluoromethyl)benzylidene)cyclopentanone | 1261266-23-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (2E,5E)-2,5-bis(2-fluoro-6-(trifluoromethyl)benzylidene)cyclopentanone
• 英文别名: (2E,5E)-2,5-bis[2-fluoro-6-(trifluoromethyl)benzylidene]cyclopentanone；2,5-Bis((E)-2-fluoro-6-(trifluoromethyl)benzylidene)cyclopentan-1-one；(2E,5E)-2,5-bis[[2-fluoro-6-(trifluoromethyl)phenyl]methylidene]cyclopentan-1-one
• CAS: 1261266-23-2
• 化学式: C₂₁H₁₂F₈O
• 分子量: 432.313
• InChiKey: WOCGWUAYELXILT-WGDLNXRISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.5
• 重原子数：
  30
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为产物：
  描述：

  2-氟-6-(三氟甲基)苯甲醛 、 环戊酮 在 potassium hydroxide 作用下， 以 乙醇 为溶剂， 反应 1.16h， 以66.3%的产率得到(2E,5E)-2,5-bis(2-fluoro-6-(trifluoromethyl)benzylidene)cyclopentanone
  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 and anti-inflammatory evaluation of novel mono-carbonyl analogues of curcumin in LPS-stimulated RAW 264.7 macrophages
  作者：Chengguang Zhao、Yuepiao Cai、Xuzhi He、Jianling Li、Li Zhang、Jianzhang Wu、Yunjie Zhao、Shulin Yang、Xiaokun Li、Wulan Li、Guang Liang

  DOI：10.1016/j.ejmech.2010.09.037

  日期：2010.12

  Curcumin is a multifunctional natural product with regulatory effects on inflammation. However, a major limitation for the application of curcumin is its poor bioavailability. We previously demonstrated that the mono-carbonyl analogues of curcumin possessed improved pharmacokinetic profiles. In this study, 33 novel mono-carbonyl analogues of curcumin were synthesized and their inhibition against TNF-alpha and IL-6 release was evaluated in LPS-stimulated RAW 264.7 macrophages. Based on the screening data, quantitative structure activity relationship was conducted, indicating that electron-withdrawing groups in benzene ring are favourable to anti-inflammatory activities of B-class compounds. Furthermore, compounds AN1 and 1382 demonstrated anti-inflammatory abilities in a dose-dependent manner. These raise the possibility that these compounds might serve as potential agents for the treatment of inflammatory diseases. (C) 2010 Elsevier Masson SAS. All rights reserved.