N-<2-(3,4-dimethoxyphenyl)-ethyl>-2-(hydroxymethyl)-phenylacetamide | 32255-42-8

• 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-<2-(3,4-dimethoxyphenyl)-ethyl>-2-(hydroxymethyl)-phenylacetamide
• 英文别名: N-[2-(3,4-dimethoxyphenyl)ethyl]-2-[2-(hydroxymethyl)phenyl]acetamide
• CAS: 32255-42-8
• 化学式: C₁₉H₂₃NO₄
• 分子量: 329.396
• InChiKey: UBPACCQIVAYDGD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  24
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  67.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-<2-(3,4-dimethoxyphenyl)-ethyl>-2-(hydroxymethyl)-phenylacetamide 在 sodium tetrahydroborate 、 三氯氧磷 作用下， 生成 2,3-dimethoxyberbine
  参考文献：
  名称：

  Syntheses of (±)-2,3-Dimethoxyberbine, (±)-Norcoralydine, and (±)-Demethoxycarbonyldihydrogambirtannine

  摘要：

  DOI：

  10.1055/s-1981-29611
• 作为产物：
  描述：

  3-异色酮 、 3,4-二甲氧基苯乙胺 以 乙醇 为溶剂， 反应 20.0h， 以77%的产率得到N-<2-(3,4-dimethoxyphenyl)-ethyl>-2-(hydroxymethyl)-phenylacetamide
  参考文献：
  名称：

  Syntheses of (±)-2,3-Dimethoxyberbine, (±)-Norcoralydine, and (±)-Demethoxycarbonyldihydrogambirtannine

  摘要：

  DOI：

  10.1055/s-1981-29611

文献信息

• Synthesis and preliminary pharmacological evaluation of 5-Hydroxy- and 5,6-dihydroxy-1,2,3,7,12,12a-hexahydrobenzo[5,6]cyclohepta[1,2,3-ij]isoquinoline derivatives as dopamine receptor ligands
  作者：Gian Mario Cingolani、Antonio Di Stefano、Fabrizio Napolitani、Barbara Mosciatti、Gianfabio Giorgioni、Nunzia Cinone、Luigi Brunetti、Grazia Luisi、Barbara Michelotto、Giustino Orlando、Barbara Costa、Antonio Lucacchini、Claudia Martini、Francesco Claudi

  DOI：10.1016/s0968-0896(01)00016-5

  日期：2001.6

  A series of 5-hydroxy- and 5,6-dihydroxy- 1,2,3,7,12,12a-hexahydrobenzo[5,6]cyclohepta[1,2,3-iJ]isoquinoline derivatives (5a-e and 6a-e) were synthesized as conformationally rigid analogues of 1-benzyltetrahydroisoquinoline and evaluated for their affinity at D-1 and D-2 dopamine receptors. All compounds showed lower D1 and D affinities than dopamine. The 5-hydroxy-1-methyl-2,3,12,12a-hexahydrobenzo[5,6]cyclohepta[1,2,3-ij] 5a and the 5,6dihydroxy analogue 6a showed D-2 agonist activity. This was proved by their effects on prolactin release from primary cultures of rat anterior pituitary cells. Molecular modeling studies showed that the geometric parameters (namely the distances from meta and para hydroxyl oxygens to the nitrogen and the height of nitrogen from the hydroxylated phenyl ring plane) of the dopaminergic pharmacophore embedded in our compounds have lower values in comparison with those observed in D-1 and D-2 selective ligands. (C) 2001 Elsevier Science Ltd. All rights reserved.
• Syntheses of (±)-2,3-Dimethoxyberbine, (±)-Norcoralydine, and (±)-Demethoxycarbonyldihydrogambirtannine
  作者：Asima Chatterjee、Somnath Ghosh

  DOI：10.1055/s-1981-29611

  日期：——