N-(3,4-Dimethoxyphenylethyl)-3,4-dimethoxy-2-hydroxymethylphenyl-acetamide | 79809-15-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: N-(3,4-Dimethoxyphenylethyl)-3,4-dimethoxy-2-hydroxymethylphenyl-acetamide
• 英文别名: N-<2-(3,4-dimethoxyphenyl)ethyl>(3,4-dimethoxy-2-hydroxymethyl)-phenylacetamide；N-[2-(3,4-dimethoxyphenyl)ethyl]-2-(hydroxymethyl)-3,4-dimethoxybenzeneacetamide；N-[2-(3,4-dimethoxyphenyl)ethyl]-2-[2-(hydroxymethyl)-3,4-dimethoxyphenyl]acetamide
• CAS: 79809-15-7
• 化学式: C₂₁H₂₇NO₆
• 分子量: 389.448
• InChiKey: WRAHNOWILUTXJU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  28
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  86.2
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  N-(3,4-Dimethoxyphenylethyl)-3,4-dimethoxy-2-hydroxymethylphenyl-acetamide 在 sodium tetrahydroborate 、 五氯化磷 作用下， 生成 延胡索乙素
  参考文献：
  名称：

  Synthesis of 7,8-dimethoxy and 7,8-methylenedioxy isochroman-3-ones an efficient synthesis of (±) tetrahydropalmatine and (±) canadine

  摘要：

  DOI：

  10.1016/s0040-4039(01)90555-6
• 作为产物：
  描述：

  N,N-dimethyl-3,4-dimethoxybenzylamine 在 正丁基锂 作用下， 以 乙醚 、 乙醇 为溶剂， 反应 21.0h， 生成 N-(3,4-Dimethoxyphenylethyl)-3,4-dimethoxy-2-hydroxymethylphenyl-acetamide
  参考文献：
  名称：

  Synthesis of 7,8-dimethoxy and 7,8-methylenedioxy isochroman-3-ones an efficient synthesis of (±) tetrahydropalmatine and (±) canadine

  摘要：

  DOI：

  10.1016/s0040-4039(01)90555-6

文献信息

• Asymmetric total synthesis and identification of tetrahydroprotoberberine derivatives as new antipsychotic agents possessing a dopamine D1, D2 and serotonin 5-HT1A multi-action profile
  作者：Haifeng Sun、Liyuan Zhu、Huicui Yang、Wangke Qian、Lin Guo、Shengbin Zhou、Bo Gao、Zeng Li、Yu Zhou、Hualiang Jiang、Kaixian Chen、Xuechu Zhen、Hong Liu

  DOI：10.1016/j.bmc.2012.12.016

  日期：2013.2

  An effective and rapid method for the microwave-assisted preparation of the key intermediate for the total synthesis of tetrahydroprotoberberines (THPBs) including l-stepholidine (l-SPD) was developed. Thirty-one THPB derivatives with diverse substituents on A and D ring were synthesized, and their binding affinity to dopamine D1, D2 and serotonin 5-HT1A and 5-HT2A receptors were determined. Compounds

  开发了一种有效且快速的微波辅助制备关键中间体的关键方法，该中间体用于全合成包括1- Stepholidine（1- SPD）的四氢小pro碱（THPBs）。合成了31个在A和D环上具有不同取代基的THPB衍生物，并测定了它们与多巴胺D 1，D 2和5-羟色胺5-HT 1A和5-HT 2A受体的结合亲和力。化合物18k和18m被确定为D 1受体的部分激动剂，K i值分别为50和6.3 nM，而两种化合物均充当D 2。受体拮抗剂（分别为K i  = 305和145 nM）和5-HT 1A受体完全激动剂（分别为K i  = 149和908 nM）。这两种THPBs化合物在动物模型中发挥了抗精神病作用。在完整动物中采用单单位记录的进一步电生理研究表明，18k兴奋的多巴胺能（DA）神经元与其5-HT 1A受体激动活性有关。这些结果表明，靶向多种神经递质受体的这两种化合物可能会提供具有新药理学特征的新型先导药物，用于治疗精神分裂症。
• Asymmetric total synthesis of tetrahydroprotoberberine derivatives and evaluation of their binding affinities at dopamine receptors
  作者：David Y.W. Lee、Jing Liu、Shuzhen Zhang、Peng Huang、Lee-Yuan Liu-Chen

  DOI：10.1016/j.bmcl.2017.01.090

  日期：2017.3

  Cocaine addiction remains a serious challenge for clinical and medical research because there is no effective pharmacological treatment. L-THP, a natural product isolated from Corydalis yanhusuo W.T. Wang, is one of the most frequently used traditional herbs to treat drug addiction in China. Our laboratory first reported that its demethylated metabolites L-ICP, L-CD, and L-CP had high affinity at dopamine D1, D2, and D5 receptors. Here we report the chemical synthesis of these metabolites and other derivatives and their binding affinities at dopamine receptors. The synthesis of these bioactive metabolites will allow further in vivo study of their potential in treating cocaine addiction. (C) 2017 Published by Elsevier Ltd.
• Synthesis and sedative properties of dl-tetrahydropalmatine
  作者：V. I. Vinogradova、M. S. Yunusov、Zh. Rezhepov、F. F. Sadritdinov

  DOI：10.1007/bf00765242

  日期：1983.1
• Synthetic application of lithiation reactions—XVI
  作者：N.S. Narasimhan、R.S. Mali、B.K. Kulkarni

  DOI：10.1016/s0040-4020(01)91915-5

  日期：1983.1
• Synthesis of 7,8-dimethoxy and 7,8-methylenedioxy isochroman-3-ones an efficient synthesis of (±) tetrahydropalmatine and (±) canadine
  作者：N.S. Narasimhan、R.S. Mali、B.K. Kulkarni

  DOI：10.1016/s0040-4039(01)90555-6

  日期：1981.1