1-(3,4,5-trimethoxyphenyl)-9-ethyl-β-carboline-3-carboxylic acid | 1145668-34-3

• 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-trimethoxyphenyl)-9-ethyl-β-carboline-3-carboxylic acid
• 英文别名: ethyl 1-(3,4,5-trimethoxy)phenyl-9-ethyl-β-carboline-3-carboxylic acid；9-Ethyl-1-(3,4,5-trimethoxyphenyl)pyrido[3,4-b]indole-3-carboxylic acid
• CAS: 1145668-34-3
• 化学式: C₂₃H₂₂N₂O₅
• 分子量: 406.438
• InChiKey: IDSXIHLLYZAHEN-UHFFFAOYSA-N

物化性质

• 熔点：
  215-216 °C
• 沸点：
  572.9±50.0 °C(predicted)
• 密度：
  1.29±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  30
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  82.8
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  1,6-二溴己烷 、 1-(3,4,5-trimethoxyphenyl)-9-ethyl-β-carboline-3-carboxylic acid 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 10.0h， 以67%的产率得到1,6-bis[1-(3,4,5-trimethoxyphenyl)-9-ethyl-β-carboline-3-carboxylic acid] hexanediyl ester
  参考文献：
  名称：

  Synthesis and biological evaluation of novel bivalent β-carbolines as potential antitumor agents

  摘要：

  一系列具有3-羧基氧之间间隔的双价β-咔啉类化合物被合成，并评估了它们的体外细胞毒活性和体内抗肿瘤效果。化合物22对小鼠Lewis肺癌表现出强效的抗肿瘤活性，肿瘤抑制率为64.2%。

  DOI：

  10.1039/c4md00098f
• 作为产物：
  描述：

  ethyl 1-(3,4,5-trimethoxy)phenyl-9-ethyl-β-carboline-3-carboxylate 在 sodium hydroxide 、 水 、 盐酸 作用下， 以 乙醇 为溶剂， 反应 1.0h， 以94%的产率得到1-(3,4,5-trimethoxyphenyl)-9-ethyl-β-carboline-3-carboxylic acid
  参考文献：
  名称：

  Synthesis and in vitro cytotoxic evaluation of novel 3,4,5-trimethoxyphenyl substituted β-carboline derivatives

  摘要：

  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.

  DOI：

  10.1016/j.ejmech.2008.03.030