3-(3-methoxyphenyl)-8-methyl-2-oxo-2H-chromene-6-carbaldehyde

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 异黄酮类化合物
• 英文名称: 3-(3-methoxyphenyl)-8-methyl-2-oxo-2H-chromene-6-carbaldehyde
• 英文别名: 3-(2-Methoxyphenyl)-8-methyl-2-oxochromene-6-carbaldehyde
• 化学式: C₁₈H₁₄O₄
• 分子量: 294.307
• InChiKey: BDXMXQFJHFYMJC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  2-甲氧基苯乙酸 、 5-甲基-4-羟基苯-1,3-二甲醛 在 N,N'-二环己基碳二亚胺 作用下， 以 二甲基亚砜 为溶剂， 反应 24.0h， 以64%的产率得到3-(3-methoxyphenyl)-8-methyl-2-oxo-2H-chromene-6-carbaldehyde
  参考文献：
  名称：

  Discovery and synthesis of novel 3-phenylcoumarin derivatives as antidepressant agents

  摘要：

  A series of 3-phenylcoumarins were synthesized and screened for potential antidepressant activity by tail suspension test (TST) in mice. Three compounds (6, 7 and 13) exhibited impressive antidepressant activity, measured in terms of percentage decrease in immobility duration (% DID). In addition, the active antidepressant compounds were subsequently studied at their most effective dose and activity of these compounds were confirmed in forced swimming test (FST) animal model, in which the compounds at a low dose of 0.5 mg/kg significantly decreased the immobility time and exhibited greater efficacy than the reference standards fluoxetine and imipramine. The potent compounds did not show any neurotoxicity in the rotarod test and the preliminary results are promising enough to warrant further studies around this scaffold. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.02.040

文献信息

• Discovery and synthesis of novel 3-phenylcoumarin derivatives as antidepressant agents
  作者：Koneni V. Sashidhara、Abdhesh Kumar、Manavi Chatterjee、K. Bhaskara Rao、Seema Singh、Anil Kumar Verma、Gautam Palit

  DOI：10.1016/j.bmcl.2011.02.040

  日期：2011.4

  A series of 3-phenylcoumarins were synthesized and screened for potential antidepressant activity by tail suspension test (TST) in mice. Three compounds (6, 7 and 13) exhibited impressive antidepressant activity, measured in terms of percentage decrease in immobility duration (% DID). In addition, the active antidepressant compounds were subsequently studied at their most effective dose and activity of these compounds were confirmed in forced swimming test (FST) animal model, in which the compounds at a low dose of 0.5 mg/kg significantly decreased the immobility time and exhibited greater efficacy than the reference standards fluoxetine and imipramine. The potent compounds did not show any neurotoxicity in the rotarod test and the preliminary results are promising enough to warrant further studies around this scaffold. (C) 2011 Elsevier Ltd. All rights reserved.