N-[(4-hydroxy-3-methoxyphenyl)methyl]cinnamamide | 149623-07-4

• 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: N-[(4-hydroxy-3-methoxyphenyl)methyl]cinnamamide
• 英文别名: N-vanillyl-cinnamamide；N-Vanillyl-cinnamamid；Zimtsaeure-vanillylamid；(E)-N-[(4-hydroxy-3-methoxyphenyl)methyl]-3-phenylprop-2-enamide
• CAS: 149623-07-4
• 化学式: C₁₇H₁₇NO₃
• 分子量: 283.327
• InChiKey: ONVACOXORQBMCU-CSKARUKUSA-N

物化性质

• 沸点：
  549.0±50.0 °C(Predicted)
• 密度：
  1.200±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  58.6
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  vanillin oxime 在 盐酸 、 乙醚 、 sodium carbonate 、 钯 作用下， 生成 N-[(4-hydroxy-3-methoxyphenyl)methyl]cinnamamide
  参考文献：
  名称：

  Ott; Zimmermann, Justus Liebigs Annalen der Chemie, 1921, vol. 425, p. 328

  摘要：

  DOI：

文献信息

• Alkyl-substituted N-(4-hydroxy-3-methoxy-benzyl)-cinnamamides, pharmaceutical compositions and uses thereof
  申请人：Kuehnert Sven

  公开号：US20070208083A1

  公开（公告）日：2007-09-06

  para-Alkyl-substituted N-(4-hydroxy-3-methoxybenzyl)-cinnamic acid amide compounds, processes for the preparation thereof, pharmaceutical compositions containing these compounds, and the use of these compounds for treating or inhibiting specific diseases or disorders.

  para-烷基取代的N-(4-羟基-3-甲氧基苯甲基)-肉桂酸酰胺化合物，其制备方法，含有这些化合物的制药组合物以及使用这些化合物治疗或抑制特定疾病或疾病的方法。
• Jones; Pyman, Journal of the Chemical Society, 1925, vol. 127, p. 2597
  作者：Jones、Pyman

  DOI：——

  日期：——
• Induction of adiponectin by natural and synthetic phenolamides in mouse and human preadipocytes and its enhancement by docosahexaenoic acid
  作者：Yoshimitsu Yamazaki、Yasuhiro Kawano、Masami Uebayasi

  DOI：10.1016/j.lfs.2007.11.016

  日期：2008.1

  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.
• Kobayashi, Scientific Papers of the Institute of Physical and Chemical Research (Japan), vol. 6, p. 176
  作者：Kobayashi

  DOI：——

  日期：——
• PARA-ALKYL-SUBSTITUIERTE N-(4-HYDROXY-3-METHOXY-BENZYL)-ZIMTSÄEUREAMIDE UND DEREN VERWENDUNG ZUR HERSTELLUNG VON ARZNEIMITTELN
  申请人：Grünenthal GmbH

  公开号：EP1778622B1

  公开（公告）日：2010-01-13