3-ethoxycarbonyl-2-benzyl-1-methyl-β-carbolinium bromide | 1229021-12-8

• 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: 3-ethoxycarbonyl-2-benzyl-1-methyl-β-carbolinium bromide
• 英文别名: ethyl 2-benzyl-1-methyl-9H-pyrido[3,4-b]indol-2-ium-3-carboxylate;bromide
• CAS: 1229021-12-8
• 化学式: Br*C₂₂H₂₁N₂O₂
• 分子量: 425.325
• InChiKey: ADWJBDVSIMMQAW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.15
• 重原子数：
  27
• 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：
  46
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  溴甲苯 、 1-甲基-9H-吡啶并[3,4-b]吲哚-3-羧酸乙酯 以 乙酸乙酯 为溶剂， 以49%的产率得到3-ethoxycarbonyl-2-benzyl-1-methyl-β-carbolinium bromide
  参考文献：
  名称：

  Design, synthesis and 3D-QSAR of β-carboline derivatives as potent antitumor agents

  摘要：

  In a continuing effort to develop novel beta-carbolines endowed with better pharmacological profiles, a series of beta-carboline derivatives were designed and synthesized based on the previously developed SARs. Cytotoxicities in vitro of these compounds against a panel of human tumor cell lines were also investigated. The results demonstrated that the N(2)-benzylated beta-carbolinium bromides 56-60 represented the most potent compounds with IC(50) values lower than 10 mu M. The application of 3D-QSAR to these compounds explored the structural basis for their biological activities. CoMFA (q(2) = 0.513, r(2) = 0.862) and CoMSIA (q(2) = 0.503, r(2) = 0.831) models were developed for a set of 47 beta-carbolines. The results indicated that the antitumor pharmacophore of these molecules were marked at position-1, -2, -3, -7 and -9 of beta-carboline ring.

  DOI：

  10.1016/j.ejmech.2010.02.036

文献信息

• Design, synthesis and 3D-QSAR of β-carboline derivatives as potent antitumor agents
  作者：Rihui Cao、Xiangdong Guan、Buxi Shi、Zhiyong Chen、Zhenhua Ren、Wenlie Peng、Huacan Song

  DOI：10.1016/j.ejmech.2010.02.036

  日期：2010.6

  In a continuing effort to develop novel beta-carbolines endowed with better pharmacological profiles, a series of beta-carboline derivatives were designed and synthesized based on the previously developed SARs. Cytotoxicities in vitro of these compounds against a panel of human tumor cell lines were also investigated. The results demonstrated that the N(2)-benzylated beta-carbolinium bromides 56-60 represented the most potent compounds with IC(50) values lower than 10 mu M. The application of 3D-QSAR to these compounds explored the structural basis for their biological activities. CoMFA (q(2) = 0.513, r(2) = 0.862) and CoMSIA (q(2) = 0.503, r(2) = 0.831) models were developed for a set of 47 beta-carbolines. The results indicated that the antitumor pharmacophore of these molecules were marked at position-1, -2, -3, -7 and -9 of beta-carboline ring.