[4-[(E)-3-[2-(1H-indol-3-yl)ethylamino]-3-oxoprop-1-enyl]-2-methoxyphenyl] acetate | 1027893-20-4

• 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: [4-[(E)-3-[2-(1H-indol-3-yl)ethylamino]-3-oxoprop-1-enyl]-2-methoxyphenyl] acetate
• CAS: 1027893-20-4
• 化学式: C₂₂H₂₂N₂O₄
• 分子量: 378.428
• InChiKey: TUQBLQVSUASTCI-CSKARUKUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  28
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  80.4
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  [4-[(E)-3-[2-(1H-indol-3-yl)ethylamino]-3-oxoprop-1-enyl]-2-methoxyphenyl] acetate 在 potassium carbonate 作用下， 以 甲醇 为溶剂， 反应 20.0h， 以100%的产率得到(E)-N-[2-(3-吲哚基)乙基]-3-(3-甲氧基-4-羟基苯基)丙烯酰胺
  参考文献：
  名称：

  肉桂酸衍生物作为抗动脉粥样硬化剂的设计，合成和药理特性评估。

  摘要：

  已合成了一系列肉桂酸和膦肉桂酸衍生物，并研究了它们抑制细胞介导的LDL氧化和氧化的LDL诱导的细胞毒性的能力。包围芳环必要的4-OH基团的供电子取代基显示出最佳结果。在测试的不同系列中，酰胺1，硫代酯5c，膦酸酯7c和氟代膦酸酯类似物12c对由培养的人微血管内皮细胞（HMEC-1）介导的LDL氧化（以及随后的毒性）表现出有效的抑制作用，具有可比的功效与普罗布考观察到的情况相同。除了这种间接的保护作用外，这些化合物还对HMEC-1中先前氧化的LDL的毒性表现出直接的保护作用。

  DOI：

  10.1021/jm050454c
• 作为产物：
  描述：

  色胺 、 4-乙酰氧基-3-甲氧基肉桂酰氯 在 吡啶 作用下， 以 甲苯 为溶剂， 生成 [4-[(E)-3-[2-(1H-indol-3-yl)ethylamino]-3-oxoprop-1-enyl]-2-methoxyphenyl] acetate
  参考文献：
  名称：

  Induction of adiponectin by natural and synthetic phenolamides in mouse and human preadipocytes and its enhancement by docosahexaenoic acid

  摘要：

  Adiponectin, the adipose-derived cytokine, plays an important role in preventing metabolic syndromes. To develop new adiponectin inducers, eight species of ferulic esters and amides, and five related compounds were synthesized and tested on the stimulation of adiponectin production in mouse 3T3-L1 and normal human preadipocytes. The ferulamides with an aromatic ring in the N-substituent are very active in inducing adiponectin as compared with the known active compounds, curcumin, [6]-gingerol, and capsaicin, and furthermore the activities of these ferulamides are remarkably stronger than those of the corresponding esters or the straight chain octylamide. The most active compound, N-(2-phenylethyl)ferulamide (7), was found to activate the PPAR (peroxisome proliferator-activated receptor) gamma-RXR (retinoid X receptor) alpha heterodimeric complex in the PPRE (PPAR-responsive element)-driven luciferase reporter assay. The adiponectin production by 7 is synergistically enhanced by coaddition of a PPAR-gamma-specific agonist, pioglitazone (PGZ), or another PPAR gamma agonist, docosahexaenoic acid (DRA), in cultured preadipocytes. The compound 7 alone did not show a statistically significant effect on the plasma adiponectin level in KK-A(y)/Ta mice, while 1% 7 in the diets significantly lowered the blood glucose and triglyceride levels and 0.3% 7 mixed with DHA oil in the diets significantly increased the adiponectin level as compared with the control. These results suggest that the present ferulamides would be useful lead compounds in developing more potent agents for treatment of metabolic syndromes through promoting the endogenous adiponectin production, and that such an activity is possibly enhanced by the coadministration with DHA. (C) 2007 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.lfs.2007.11.016