1-(3,4,5-trimethoxy)phenyl-9-methyl-β-carboline-3-carboxaldehyde | 1145668-27-4

• 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-(3,4,5-trimethoxy)phenyl-9-methyl-β-carboline-3-carboxaldehyde
• 英文别名: 9-methyl-1-(3,4,5-trimethoxyphenyl)-β-carboline-3-carbaldehyde；9-Methyl-1-(3,4,5-trimethoxyphenyl)pyrido[3,4-b]indole-3-carbaldehyde
• CAS: 1145668-27-4
• 化学式: C₂₂H₂₀N₂O₄
• 分子量: 376.412
• InChiKey: CBSSJGZQVPOZFK-UHFFFAOYSA-N

物化性质

• 熔点：
  200-201 °C
• 沸点：
  508.7±50.0 °C(predicted)
• 密度：
  1.24±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  28
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  62.6
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  N,N-二乙基丁烷-1,4-二胺 、 1-(3,4,5-trimethoxy)phenyl-9-methyl-β-carboline-3-carboxaldehyde 以 甲醇 、 二氯甲烷 为溶剂， 生成
  参考文献：
  名称：

  Synthesis, cytotoxic activities and DNA binding properties of β-carboline derivatives

  摘要：

  In a continuing effort to develop novel beta-carbolines endowed with better pharmacological profile, a series of water-soluble beta-carbolines bearing a flexible amino side chain was designed and synthesized, and the cytotoxic activities in vitro of these compounds were evaluated. The N-9-arylated alkyl substituted beta-carbolines represented the most interesting cytotoxic agents, and compounds 4c and 4d were found to be the most potent compounds with IC50 values lower than 10 mu M against ten human tumor cell lines. The results confirmed that the N-9-arylated alkyl substituents of beta-carboline played a very important role in the modulation of the cytotoxic potencies. In addition, the interaction with DNA of these compounds was also investigated, these compounds were found to exhibit significant DNA binding affinity. (C) 2010 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2010.07.037
• 作为产物：
  描述：

  1-(3,4,5-trimethoxy)phenyl-3-hydroxymethyl-9-methyl-β-carboline 在 manganese(IV) oxide 作用下， 以 乙腈 为溶剂， 反应 2.0h， 以74%的产率得到1-(3,4,5-trimethoxy)phenyl-9-methyl-β-carboline-3-carboxaldehyde
  参考文献：
  名称：

  Synthesis and biological evaluation of piperazine group-linked bivalent β-carbolines as potential antitumor agents

  摘要：

  一系列具有3-亚甲基单元之间的哌嗪基间隔的二价β-咔啉类化合物被合成，并评估了它们的体外细胞毒活性。化合物7e和7g表现出强大的细胞毒活性。

  DOI：

  10.1039/c5md00312a

文献信息

• Synthesis and in vitro cytotoxic evaluation of novel 3,4,5-trimethoxyphenyl substituted β-carboline derivatives
  作者：Qifeng Wu、Rihui Cao、Manxiu Feng、Xiangdong Guan、Chunming Ma、Jinbing Liu、Huacan Song、Wenlie Peng

  DOI：10.1016/j.ejmech.2008.03.030

  日期：2009.2

  To elucidate further our SARs' study on the chemistry and cytotoxic activity and probe the structural requirement for the potent antitumor activity of beta-carbolines, a series of novel 1,9-disubstituted and 1,3,9-trisubstituted beta-carboline derivatives were designed and synthesized from the starting material L-tryptophan and 3,4,5-trimethoxybenezaldehyde. Cytotoxic activities of these compounds in vitro were investigated, and the SARs associated with position-1, 3 and 9 substituents in beta-carbolines have also been discussed. It has been observed that these compounds only displayed moderate to weak cytotoxic activities. Interestingly, most of the investigated compounds displayed selectively cytotoxic activities to human BCG-823 cell lines with IC50 value lower than 100 mu M. In addition, the short alkyl substituents in position-9 increased the cytotoxic activities with the tendency of n-butyl > ethyl > methyl. These data confirmed that (1) an alkyl substituent at position-9 of beta-carboline nucleus plays an important role in determining their antitumor activities; (2) different beta-carbolines bearing various substituents in beta-carboline nucleus interacted selectively with specific targets leading to the difference of biochemical and pharmacological effects. (C) 2008 Elsevier Masson SAS. All fights reserved.
• Synthesis and biological evaluation of piperazine group-linked bivalent β-carbolines as potential antitumor agents
  作者：Rongqin Sun、Rui Liu、Chi Zhou、Zhenghua Ren、Liang Guo、Qin Ma、Wenxi Fan、Liqin Qiu、Huijuan Yu、Guang Shao、Rihui Cao

  DOI：10.1039/c5md00312a

  日期：——

  A series of bivalent β-carbolines with a piperazine group spacer between 3-methylene units were synthesized and their cytotoxic activities in vitro were evaluated. Compounds 7e and 7g exhibited potent cytotoxic activity.

  一系列具有3-亚甲基单元之间的哌嗪基间隔的二价β-咔啉类化合物被合成，并评估了它们的体外细胞毒活性。化合物7e和7g表现出强大的细胞毒活性。
• Synthesis, cytotoxic activities and DNA binding properties of β-carboline derivatives
  作者：Zhiyong Chen、Rihui Cao、Liang Yu、Buxi Shi、Jie Sun、Liang Guo、Qin Ma、Wei Yi、Xiao Song、Huacan Song

  DOI：10.1016/j.ejmech.2010.07.037

  日期：2010.11

  In a continuing effort to develop novel beta-carbolines endowed with better pharmacological profile, a series of water-soluble beta-carbolines bearing a flexible amino side chain was designed and synthesized, and the cytotoxic activities in vitro of these compounds were evaluated. The N-9-arylated alkyl substituted beta-carbolines represented the most interesting cytotoxic agents, and compounds 4c and 4d were found to be the most potent compounds with IC50 values lower than 10 mu M against ten human tumor cell lines. The results confirmed that the N-9-arylated alkyl substituents of beta-carboline played a very important role in the modulation of the cytotoxic potencies. In addition, the interaction with DNA of these compounds was also investigated, these compounds were found to exhibit significant DNA binding affinity. (C) 2010 Elsevier Masson SAS. All rights reserved.