ethyl 9-(3,4,5-trimethoxybenzyl)-β-carboline-3-carboxylate

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: ethyl 9-(3,4,5-trimethoxybenzyl)-β-carboline-3-carboxylate
• 英文别名: Ethyl 9-[(3,4,5-trimethoxyphenyl)methyl]pyrido[3,4-b]indole-3-carboxylate；ethyl 9-[(3,4,5-trimethoxyphenyl)methyl]pyrido[3,4-b]indole-3-carboxylate
• 化学式: C₂₄H₂₄N₂O₅
• 分子量: 420.465
• InChiKey: BKUHCWHHPADIGP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  31
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  71.8
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  2,3,4,9-四氢-1H-beta-咔啉-3-甲酸 在 manganese(IV) oxide 、 氯化亚砜 、 potassium hydroxide 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 24.5h， 生成 ethyl 9-(3,4,5-trimethoxybenzyl)-β-carboline-3-carboxylate
  参考文献：
  名称：

  Synthesis and biological evaluation of novel 3,9-substituted β-carboline derivatives as anticancer agents

  摘要：

  In our previous studies on 1-benzyl-3-(5-hydroxymethyl-2-furyl) indazole (YC-1) analogs, we synthesised numerous substituted carbazole and alpha-carboline derivatives, which exhibited anticancer activity. In this study, we designed and synthesised a series of 3,9-substituted beta-carbolines, by replacing the tricyclic rings of carbazole and alpha-carboline derivatives with isosteric beta-carboline, and evaluated anticancer activity. We observed that 9-(2-methoxybenzyl)-beta-carboline-3-carboxylic acid (11a) inhibited the growth of HL-60 cells by inducing apoptosis, with a half maximal inhibitory concentration of 4.0 mu M. Our findings indicate that b-carboline derivatives can be used as lead compounds for developing novel antitumor agents. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2015.07.058

文献信息

• Synthesis and biological evaluation of novel 3,9-substituted β-carboline derivatives as anticancer agents
  作者：Yi-Fong Chen、Yi-Chien Lin、Jeng-Pang Chen、Hsu-Chin Chan、Mei-Hua Hsu、Hui-Yi Lin、Sheng-Chu Kuo、Li-Jiau Huang

  DOI：10.1016/j.bmcl.2015.07.058

  日期：2015.9

  In our previous studies on 1-benzyl-3-(5-hydroxymethyl-2-furyl) indazole (YC-1) analogs, we synthesised numerous substituted carbazole and alpha-carboline derivatives, which exhibited anticancer activity. In this study, we designed and synthesised a series of 3,9-substituted beta-carbolines, by replacing the tricyclic rings of carbazole and alpha-carboline derivatives with isosteric beta-carboline, and evaluated anticancer activity. We observed that 9-(2-methoxybenzyl)-beta-carboline-3-carboxylic acid (11a) inhibited the growth of HL-60 cells by inducing apoptosis, with a half maximal inhibitory concentration of 4.0 mu M. Our findings indicate that b-carboline derivatives can be used as lead compounds for developing novel antitumor agents. (C) 2015 Elsevier Ltd. All rights reserved.