1-(2,3-dihydrobenzo[1,4]dioxin-6-yl)-6-ethyl-2-propyl-2,3,4,9-tetrahydro-1H-β-carboline | 1310575-36-0

• 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: 1-(2,3-dihydrobenzo[1,4]dioxin-6-yl)-6-ethyl-2-propyl-2,3,4,9-tetrahydro-1H-β-carboline
• 英文别名: 1-(2,3-Dihydro-1,4-benzodioxin-6-yl)-6-ethyl-2-propyl-1,3,4,9-tetrahydropyrido[3,4-b]indole
• CAS: 1310575-36-0
• 化学式: C₂₄H₂₈N₂O₂
• 分子量: 376.499
• InChiKey: MOXQBEDVFPVIOI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  28
• 可旋转键数：
  4
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  37.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2-(5-ethyl-1H-indol-3-yl)ethylamine 在 potassium carbonate 、 三氟乙酸 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 48.0h， 生成 1-(2,3-dihydrobenzo[1,4]dioxin-6-yl)-6-ethyl-2-propyl-2,3,4,9-tetrahydro-1H-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

• 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.