n-pentyl β-carboline-1-propionate

• 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: n-pentyl β-carboline-1-propionate
• 英文别名: n-Pentyl beta-carboline-1-propionate；pentyl 3-(9H-pyrido[3,4-b]indol-1-yl)propanoate
• 化学式: C₁₉H₂₂N₂O₂
• 分子量: 310.396
• InChiKey: OXYXZGCPXAISTO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  23
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  55
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  戊醇 、 beta-咔啉-1-丙酸 在 硫酸 作用下， 反应 4.0h， 以83%的产率得到n-pentyl β-carboline-1-propionate
  参考文献：
  名称：

  Cytotoxic and Antimalarial β-Carboline Alkaloids from the Roots of Eurycoma longifolia

  摘要：

  Three new [n-pentyl beta-carboline-1-propionate (1), 5-hydroxymethyl-9-methoxycanthin-6-one (2), and 1-hydroxy-9-methoxycanthin-6-one (3)] and 19 known beta-carboline alkaloids were isolated from the roots of Eurycoma longifolia. The new structures were determined by comprehensive analyses of their 1D and 2D NMR and mass spectral data and by chemical transformation. These compounds were screened for in vitro cytotoxic and antimalarial activities, and 9-methoxycanthin-6-one (4) and canthin-6-one (5) demonstrated significant cytotoxicity against human lung cancer (A-549) and human breast cancer (MCF-7) cell lines.

  DOI：

  10.1021/np030277n

文献信息

• Cytotoxic and Antimalarial β-Carboline Alkaloids from the Roots of <i>Eurycoma longifolia</i>
  作者：Ping-Chung Kuo、Li-Shian Shi、Amooru G. Damu、Chung-Ren Su、Chieh-Hung Huang、Chih-Huang Ke、Jin-Bin Wu、Ai-Jeng Lin、Kenneth F. Bastow、Kuo-Hsiung Lee、Tian-Shung Wu

  DOI：10.1021/np030277n

  日期：2003.10.1

  Three new [n-pentyl beta-carboline-1-propionate (1), 5-hydroxymethyl-9-methoxycanthin-6-one (2), and 1-hydroxy-9-methoxycanthin-6-one (3)] and 19 known beta-carboline alkaloids were isolated from the roots of Eurycoma longifolia. The new structures were determined by comprehensive analyses of their 1D and 2D NMR and mass spectral data and by chemical transformation. These compounds were screened for in vitro cytotoxic and antimalarial activities, and 9-methoxycanthin-6-one (4) and canthin-6-one (5) demonstrated significant cytotoxicity against human lung cancer (A-549) and human breast cancer (MCF-7) cell lines.