6-ethyl-1-(3-methoxyphenyl)-1,2,3,4-tetrahydro-β-carboline

• 分子结构分类: 有机化合物 - 生物碱及其衍生物 - 哈马拉生物碱
• 英文名称: 6-ethyl-1-(3-methoxyphenyl)-1,2,3,4-tetrahydro-β-carboline
• 英文别名: 6-ethyl-1-(3-methoxyphenyl)-2,3,4,9-tetrahydro-1H-β-carboline；6-ethyl-1-(3-methoxyphenyl)-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole
• 化学式: C₂₀H₂₂N₂O
• 分子量: 306.407
• InChiKey: KBHBWNXRIOXXGU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  37
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  6-ethyl-1-(3-methoxyphenyl)-1,2,3,4-tetrahydro-β-carboline 在 10% Pd/C 、 氢气 、 盐酸 作用下， 以 甲醇 、 乙醚 、 乙酸乙酯 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 反应 72.0h， 以85%的产率得到5-ethyl-2-(3-methoxybenzyl)tryptamine hydrochloride
  参考文献：
  名称：

  通过β-咔啉的开环，温和而有效的途径获得2-苄基色胺衍生物

  摘要：

  我们分两步描述了一种温和而简便的方法，通过该方法，将多种苄基引入色胺的C-2位置。第一步包括通过Pictet-Spengler反应从色胺胺衍生物开始合成β-咔啉。通过氢化使β-咔啉开环，得到所需的2-取代的苄基色胺为吲哚产物。可以实现烷基化的补充步骤，以得到N-烷基-2-取代的苄基色胺。在这些反应过程中，氮原子不需要任何保护步骤。

  DOI：

  10.1016/j.tet.2008.07.056
• 作为产物：
  描述：

  (5-乙基-1H-吲哚-3-基)乙腈 在 lithium aluminium tetrahydride 、 三氟乙酸 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 反应 24.0h， 生成 6-ethyl-1-(3-methoxyphenyl)-1,2,3,4-tetrahydro-β-carboline
  参考文献：
  名称：

  Antioxydant activity of β-carboline derivatives in the LDL oxidation model

  摘要：

  A series of beta-carboline compounds were synthesized, starting from compound GWC22, their antioxidant activity was determined by inhibition of lipid peroxidation. The oxidation of LDL was induced in the presence of CuSO4 or 2,2'-azobis(2-amidinopropane) dihydrochloride (AAPH). The protective actions of these compounds against the cytotoxicity were evaluated with lactate dehydrogenase (LDH) activity in bovine aortic endothelial cells (BAECs) and cellular vitality by measuring mitochondrial activity in the presence of MTT (3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide). Most of compounds showed an higher antioxidant activity than GWC22 derivative (R = 1.6 for 5 mu M CuSO4). The best antioxidant activities are phenolic and benzyloxy derivatives with ratio R = 1.9 to 2.8 for 1 mu M CuSO4. These substances have protective actions and increase significantly the cell viability. (C) 2011 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2011.03.048

文献信息

• Cheve, Gwenael; Duriez, Patrick; Fruchart, Jean-Charles, Medicinal Chemistry Research, 2002, vol. 11, # 7, p. 361 - 379
  作者：Cheve, Gwenael、Duriez, Patrick、Fruchart, Jean-Charles、Teissier, Elisabeth、Poupaert, Jacques、Lesieur, Daniel

  DOI：——

  日期：——
• Antioxydant activity of β-carboline derivatives in the LDL oxidation model
  作者：Fariza Hadjaz、Soizic Besret、Françoise Martin-Nizard、Saïd Yous、Sébastien Dilly、Nicolas Lebegue、Philippe Chavatte、Patrick Duriez、Pascal Berthelot、Pascal Carato

  DOI：10.1016/j.ejmech.2011.03.048

  日期：2011.6

  A series of beta-carboline compounds were synthesized, starting from compound GWC22, their antioxidant activity was determined by inhibition of lipid peroxidation. The oxidation of LDL was induced in the presence of CuSO4 or 2,2'-azobis(2-amidinopropane) dihydrochloride (AAPH). The protective actions of these compounds against the cytotoxicity were evaluated with lactate dehydrogenase (LDH) activity in bovine aortic endothelial cells (BAECs) and cellular vitality by measuring mitochondrial activity in the presence of MTT (3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide). Most of compounds showed an higher antioxidant activity than GWC22 derivative (R = 1.6 for 5 mu M CuSO4). The best antioxidant activities are phenolic and benzyloxy derivatives with ratio R = 1.9 to 2.8 for 1 mu M CuSO4. These substances have protective actions and increase significantly the cell viability. (C) 2011 Elsevier Masson SAS. All rights reserved.
• A mild and efficient route to 2-benzyl tryptamine derivatives via ring-opening of β-carbolines
  作者：Fariza Hadjaz、Saïd Yous、Nicolas Lebegue、Pascal Berthelot、Pascal Carato

  DOI：10.1016/j.tet.2008.07.056

  日期：2008.10

  described a mild and easy method, in two steps, by which various benzyl groups were introduced in the C-2 position of tryptamine. The first step consisted on the synthesis of β-carbolines, starting from tryptamine derivatives, by a Pictet–Spengler reaction. Ring-opening of the β-carbolines, by hydrogenation, led to the desired 2-substituted benzyl tryptamine indole products. A supplementary step of alkylation

  我们分两步描述了一种温和而简便的方法，通过该方法，将多种苄基引入色胺的C-2位置。第一步包括通过Pictet-Spengler反应从色胺胺衍生物开始合成β-咔啉。通过氢化使β-咔啉开环，得到所需的2-取代的苄基色胺为吲哚产物。可以实现烷基化的补充步骤，以得到N-烷基-2-取代的苄基色胺。在这些反应过程中，氮原子不需要任何保护步骤。