(2E,5E)-2,5-bis(4-(piperidin-1-yl)benzylidene)cyclopentanone | 1261266-30-1

• 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: (2E,5E)-2,5-bis(4-(piperidin-1-yl)benzylidene)cyclopentanone
• 英文别名: (2E,5E)-2,5-bis[(4-piperidin-1-ylphenyl)methylidene]cyclopentan-1-one
• CAS: 1261266-30-1
• 化学式: C₂₉H₃₄N₂O
• 分子量: 426.602
• InChiKey: UAKDCOPDYHIDPT-CDTUYSNOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.5
• 重原子数：
  32
• 可旋转键数：
  4
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  23.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  4-哌啶-1-基-苯甲醛 、 环戊酮 在 甲醇 、 sodium methylate 作用下， 以92.9%的产率得到(2E,5E)-2,5-bis(4-(piperidin-1-yl)benzylidene)cyclopentanone
  参考文献：
  名称：

  Synthesis and anti-inflammatory evaluation of novel mono-carbonyl analogues of curcumin in LPS-stimulated RAW 264.7 macrophages

  摘要：

  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.

  DOI：

  10.1016/j.ejmech.2010.09.037

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.