1-[N-(2-diethylamino-ethyl)-aminomethyl]-9-isobutyl-β-carboline | 1325719-75-2

• 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-[N-(2-diethylamino-ethyl)-aminomethyl]-9-isobutyl-β-carboline
• 英文别名: N',N'-diethyl-N-[[9-(2-methylpropyl)pyrido[3,4-b]indol-1-yl]methyl]ethane-1,2-diamine
• CAS: 1325719-75-2
• 化学式: C₂₂H₃₂N₄
• 分子量: 352.523
• InChiKey: CXTQAMJFZZKPGB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  26
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  33.1
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-[N-(2-diethylamino-ethyl)-aminomethyl]-9-isobutyl-β-carboline 在 盐酸 作用下， 以 乙醇 为溶剂， 反应 0.5h， 生成 1-[N-(2-diethylamino-ethyl)-aminomethyl]-9-isobutyl-β-carboline tetrahydrochloride
  参考文献：
  名称：

  Synthesis and biological evaluation of 1,9-disubstituted β-carbolines as potent DNA intercalating and cytotoxic agents

  摘要：

  A series of novel 1,9-disubstituted beta-carbolines was designed, synthesized and evaluated as cytotoxic and DNA intercalating agents. Compounds 7b, 7c, 8b and 8c exhibited the most potent cytotoxic activities with IC50 values of lower than 20 mu M against ten human tumor cell lines. The results indicated that (1) the 3-chlorobenzyl and 3-phenylpropyl substituents in position-9 of beta-carboline nucleus were the suitable pharmacophoric group giving rise to significant antitumor agents; (2) the length of the alkylamino side chain moiety affected their cytotoxic potencies, and three CH2 units were more favorable. In addition, these compounds were found to exhibit remarkable DNA intercalating effects. (C) 2011 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2011.08.027
• 作为产物：
  描述：

  L-色氨酸 在 selenium(IV) oxide 、 sodium hydride 、 sodium cyanoborohydride 作用下， 以 1,4-二氧六环 、 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 26.0h， 生成 1-[N-(2-diethylamino-ethyl)-aminomethyl]-9-isobutyl-β-carboline
  参考文献：
  名称：

  Synthesis and biological evaluation of 1,9-disubstituted β-carbolines as potent DNA intercalating and cytotoxic agents

  摘要：

  A series of novel 1,9-disubstituted beta-carbolines was designed, synthesized and evaluated as cytotoxic and DNA intercalating agents. Compounds 7b, 7c, 8b and 8c exhibited the most potent cytotoxic activities with IC50 values of lower than 20 mu M against ten human tumor cell lines. The results indicated that (1) the 3-chlorobenzyl and 3-phenylpropyl substituents in position-9 of beta-carboline nucleus were the suitable pharmacophoric group giving rise to significant antitumor agents; (2) the length of the alkylamino side chain moiety affected their cytotoxic potencies, and three CH2 units were more favorable. In addition, these compounds were found to exhibit remarkable DNA intercalating effects. (C) 2011 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2011.08.027

文献信息

• Synthesis and biological evaluation of 1,9-disubstituted β-carbolines as potent DNA intercalating and cytotoxic agents
  作者：Zhiyong Chen、Rihui Cao、Buxi Shi、Liang Guo、Jie Sun、Qin Ma、Wenxi Fan、Huacan Song

  DOI：10.1016/j.ejmech.2011.08.027

  日期：2011.10

  A series of novel 1,9-disubstituted beta-carbolines was designed, synthesized and evaluated as cytotoxic and DNA intercalating agents. Compounds 7b, 7c, 8b and 8c exhibited the most potent cytotoxic activities with IC50 values of lower than 20 mu M against ten human tumor cell lines. The results indicated that (1) the 3-chlorobenzyl and 3-phenylpropyl substituents in position-9 of beta-carboline nucleus were the suitable pharmacophoric group giving rise to significant antitumor agents; (2) the length of the alkylamino side chain moiety affected their cytotoxic potencies, and three CH2 units were more favorable. In addition, these compounds were found to exhibit remarkable DNA intercalating effects. (C) 2011 Elsevier Masson SAS. All rights reserved.