(E)-1-(4-Benzylpiperidino)-3-(3,4,5-trimethoxyphenyl)-2-propen-1-one | 1360146-61-7

• 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: (E)-1-(4-Benzylpiperidino)-3-(3,4,5-trimethoxyphenyl)-2-propen-1-one
• 英文别名: (E)-1-(4-benzylpiperidin-1-yl)-3-(3,4,5-trimethoxyphenyl)prop-2-en-1-one
• CAS: 1360146-61-7
• 化学式: C₂₄H₂₉NO₄
• 分子量: 395.499
• InChiKey: ZFNPYOBLIZVUNN-MDZDMXLPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  29
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  48
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  4-苄基哌啶 、 3,4,5-三甲氧基肉桂酸 在 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 24.5h， 生成 (E)-1-(4-Benzylpiperidino)-3-(3,4,5-trimethoxyphenyl)-2-propen-1-one
  参考文献：
  名称：

  Synthesis and Evaluation of a Series of 3,4,5-Trimethoxycinnamic Acid Derivatives as Potential Antinarcotic Agents

  摘要：

  A series of 3,4,5‐trimethoxycinnamic acid derivatives was prepared and evaluated for antinarcotic effects on morphine dependence in mice and binding affinities on serotonergic receptors. The key synthetic strategies involve generation of ketones 6–7, esters 9–12 through condensation reaction, and amides 13–19 via coupling reaction using 1‐hydroxybenzotriazole/ethyl(dimethylaminopropryl)carbodiimide system in high yield. We found that the naloxone‐induced morphine withdrawal syndrome was significantly suppressed by new synthetic 3,4,5‐trimethoxycinnamic acid derivatives (20 mg/kg/day). Most of 3,4,5‐trimethoxycinnamic acid derivatives were found to have high affinity to 5‐HT1A receptor. The naloxone‐induced morphine withdrawal syndrome was attenuated by (+)8‐OH‐DPAT (0.1 mg/kg/day, i.p.), a 5‐HT1A receptor agonist. In cortical neuronal cells, (+)8‐OH‐DPAT (1 μm) produced an elevation of the pERK 1/2 expression, and the elevated pERK levels were inhibited by WAY 100635, a 5‐HT1A receptor‐specific antagonist. Interestingly, the pERK levels were increased by the 3,4,5‐trimethoxycinnamic acid derivatives and the derivatives‐mediated changes in pERK levels were blocked by the WAY 100635. These results suggested that new synthetic 3,4,5‐trimethoxycinnamic acid derivatives have a potential antinarcotic effect through acting as a 5‐HT1A receptor agonist in mice.

  DOI：

  10.1111/cbdd.12087

文献信息

• Synthesis and Evaluation of a Series of 3,4,5-Trimethoxycinnamic Acid Derivatives as Potential Antinarcotic Agents
  作者：Jae-Chul Jung、Sohyeon Moon、Dongguk Min、Woo Kyu Park、Mankil Jung、Seikwan Oh

  DOI：10.1111/cbdd.12087

  日期：2013.3

  A series of 3,4,5‐trimethoxycinnamic acid derivatives was prepared and evaluated for antinarcotic effects on morphine dependence in mice and binding affinities on serotonergic receptors. The key synthetic strategies involve generation of ketones 6–7, esters 9–12 through condensation reaction, and amides 13–19 via coupling reaction using 1‐hydroxybenzotriazole/ethyl(dimethylaminopropryl)carbodiimide system in high yield. We found that the naloxone‐induced morphine withdrawal syndrome was significantly suppressed by new synthetic 3,4,5‐trimethoxycinnamic acid derivatives (20 mg/kg/day). Most of 3,4,5‐trimethoxycinnamic acid derivatives were found to have high affinity to 5‐HT1A receptor. The naloxone‐induced morphine withdrawal syndrome was attenuated by (+)8‐OH‐DPAT (0.1 mg/kg/day, i.p.), a 5‐HT1A receptor agonist. In cortical neuronal cells, (+)8‐OH‐DPAT (1 μm) produced an elevation of the pERK 1/2 expression, and the elevated pERK levels were inhibited by WAY 100635, a 5‐HT1A receptor‐specific antagonist. Interestingly, the pERK levels were increased by the 3,4,5‐trimethoxycinnamic acid derivatives and the derivatives‐mediated changes in pERK levels were blocked by the WAY 100635. These results suggested that new synthetic 3,4,5‐trimethoxycinnamic acid derivatives have a potential antinarcotic effect through acting as a 5‐HT1A receptor agonist in mice.