3,5-bis((1H-indol-5-yl)methylene)piperidin-4-one | 1312614-68-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: 3,5-bis((1H-indol-5-yl)methylene)piperidin-4-one
• 英文别名: (3E,5E)-3,5-bis(1H-indol-5-ylmethylidene)piperidin-4-one
• CAS: 1312614-68-8
• 化学式: C₂₃H₁₉N₃O
• 分子量: 353.423
• InChiKey: NFOLRBRNBDZTTR-AYKLPDECSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  27
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  60.7
• 氢给体数：
  3
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  5-吲哚甲醛 、 4-氧代哌啶酮盐酸盐 在 盐酸 、 溶剂黄146 、 potassium carbonate 作用下， 以 水 、 丙酮 为溶剂， 反应 0.5h， 以82%的产率得到3,5-bis((1H-indol-5-yl)methylene)piperidin-4-one
  参考文献：
  名称：

  Curcumin analogues as possible anti-proliferative & anti-inflammatory agents

  摘要：

  A series of novel curcumin analogues has been designed, synthesized and tested in vitro/in vivo as potential multi-target agents. Their anti-proliferative and anti-inflammatory activities were studied. Compounds 1b and 2b were stronger inhibitors of soybean lipoxygenase (LOX) than curcumin. Analogue 1b was also the most potent aldose reductase (ALR2) inhibitor. Two compounds, (1a and 1f) exhibited in vivo anti-inflammatory activity comparable to that of indomethacin, whereas derivative 1i exhibited even higher activity. The derivatives were also tested for their anti-proliferative activity using three different human cancer cell lines. Compounds 1a, 1b, 1d and 2b exhibited significant growth inhibitory activity as compared to curcumin, against all three cancer cell lines. Lipophilicity was determined as R-M values using RPTLC and theoretically. The results are discussed in terms of the structural characteristics of the compounds. Docking simulations were performed on LOX and ALR2 inhibitor 1b and curcumin. Compound 1b is well fitted in the active site of ALR2, binding to the ALR2 enzyme in a similar way to curcumin. Allosteric interactions may govern the LOX-inhibitor binding. (C) 2011 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2011.03.060

文献信息

• Curcumin analogues as possible anti-proliferative & anti-inflammatory agents
  作者：A.-M. Katsori、M. Chatzopoulou、K. Dimas、C. Kontogiorgis、A. Patsilinakos、T. Trangas、D. Hadjipavlou-Litina

  DOI：10.1016/j.ejmech.2011.03.060

  日期：2011.7

  A series of novel curcumin analogues has been designed, synthesized and tested in vitro/in vivo as potential multi-target agents. Their anti-proliferative and anti-inflammatory activities were studied. Compounds 1b and 2b were stronger inhibitors of soybean lipoxygenase (LOX) than curcumin. Analogue 1b was also the most potent aldose reductase (ALR2) inhibitor. Two compounds, (1a and 1f) exhibited in vivo anti-inflammatory activity comparable to that of indomethacin, whereas derivative 1i exhibited even higher activity. The derivatives were also tested for their anti-proliferative activity using three different human cancer cell lines. Compounds 1a, 1b, 1d and 2b exhibited significant growth inhibitory activity as compared to curcumin, against all three cancer cell lines. Lipophilicity was determined as R-M values using RPTLC and theoretically. The results are discussed in terms of the structural characteristics of the compounds. Docking simulations were performed on LOX and ALR2 inhibitor 1b and curcumin. Compound 1b is well fitted in the active site of ALR2, binding to the ALR2 enzyme in a similar way to curcumin. Allosteric interactions may govern the LOX-inhibitor binding. (C) 2011 Elsevier Masson SAS. All rights reserved.