2-Benzyl-1-methyl-7-pentan-3-yloxy-9-(3-phenylpropyl)pyrido[3,4-b]indol-2-ium;bromide | 1015792-15-0

• 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: 2-Benzyl-1-methyl-7-pentan-3-yloxy-9-(3-phenylpropyl)pyrido[3,4-b]indol-2-ium;bromide
• 英文别名: 2-benzyl-1-methyl-7-pentan-3-yloxy-9-(3-phenylpropyl)pyrido[3,4-b]indol-2-ium;bromide
• CAS: 1015792-15-0
• 化学式: Br*C₃₃H₃₇N₂O
• 分子量: 557.574
• InChiKey: BIACKIXQOURAML-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  4.64
• 重原子数：
  37
• 可旋转键数：
  10
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  18
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  肉叶云香碱 在 氢溴酸 、 sodium hydride 、 溶剂黄146 作用下， 以 乙酸乙酯 、 N,N-二甲基甲酰胺 为溶剂， 生成 2-Benzyl-1-methyl-7-pentan-3-yloxy-9-(3-phenylpropyl)pyrido[3,4-b]indol-2-ium;bromide
  参考文献：
  名称：

  Synthesis and structure–activity relationships of harmine derivatives as potential antitumor agents

  摘要：

  Harmine, a naturally occurring beta-carboline alkaloid, showed good antitumor activities together with remarkable neurotoxic effects in animal models. In order to search for novel leading compounds endowed with better antitumor activities and less neurotoxicities, a series of harmine derivatives were designed and synthesized by modification of position-2, 7 and 9 of beta-carboline nucleus, and their cytotoxic activities against human tumor cell lines were investigated. Acute toxicities and antitumor activities of the selected compounds in mice were also evaluated. Structure activity relationships studies confirmed that (1) the 7-methoxy structural moiety was the pharmacophore responsible for the neurotoxic effects of this class of compounds; (2) the substituents in position-2 and 9 played a vital role in modulation of their antitumor activities. (C) 2012 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2012.11.045

文献信息

• Synthesis and structure–activity relationships of N2-alkylated quaternary β-carbolines as novel antitumor agents
  作者：Guoxian Zhang、Rihui Cao、Liang Guo、Qin Ma、Wenxi Fan、Xuemei Chen、Jianru Li、Guang Shao、Liqin Qiu、Zhenghua Ren

  DOI：10.1016/j.ejmech.2013.04.031

  日期：2013.7

  A series of novel N-2-alkylated quaternary beta-carbolines was synthesized by modification of position-1, 2,7 and 9 of beta-carboline nucleus with various alkyl and arylated alkyl substituents, and their cytotoxic activities in vitro and antitumor potencies in mice were evaluated. Compound 3m was found to be the most potent antitumor agent. SARs analysis revealed that (1) the substituents in position-2 and 9 of beta-carboline nucleus played a vital role in modulation of antitumor activity; (2) the benzyl and 3-phenylpropyl substituents in position-2 and 9 of beta-carboline ring were the optimal substituents giving rise to significant antitumor agent. These compounds might be a novel promising class of antitumor agents with clinical development potential. (C) 2013 Elsevier Masson SAS. All rights reserved.