2-(4-chlorobenzyl)-7-((4-chlorobenzyl)oxy)-1-methyl-9H-pyrido[3,4-b]indol-2-ium bromide

• 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-(4-chlorobenzyl)-7-((4-chlorobenzyl)oxy)-1-methyl-9H-pyrido[3,4-b]indol-2-ium bromide
• 英文别名: 7-[(4-chlorophenyl)methoxy]-2-[(4-chlorophenyl)methyl]-1-methyl-9H-pyrido[3,4-b]indol-2-ium;bromide
• 化学式: Br*C₂₆H₂₁Cl₂N₂O
• 分子量: 528.276
• InChiKey: OEFNCLBQZYNEKP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.86
• 重原子数：
  32
• 可旋转键数：
  5
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  28.9
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  哈尔酚 在 caesium carbonate 作用下， 以 乙酸乙酯 、 N,N-二甲基甲酰胺 、 异丙醇 为溶剂， 反应 28.0h， 生成 2-(4-chlorobenzyl)-7-((4-chlorobenzyl)oxy)-1-methyl-9H-pyrido[3,4-b]indol-2-ium bromide
  参考文献：
  名称：

  Exploiting the Polypharmacology of ß-Carbolines to Disrupt O. volvulus Molting

  摘要：

  Onchocerciasis is an infection caused by the filarial worm Onchocerca volvulus, which can eventually result in blindness. The lack of an effective macrofilaricide and the possible development of ivermectin-resistant strains of O. volvulus necessitate the, need for alternative treatment strategies. We have shown that targeting the L3-stagespecific chitinase OvCHT1 impairs the shedding of the filarial cuticle. In our continued efforts to discover OvCHT1 inhibitors, we identified the beta-carboline alkaloid scaffolding as a chitinase inhibitor that is capable of penetrating the worm cuticle. Herein, we disclose the rich polypharmacology of the beta-carboline class of compounds as an approach to abrogate the molting of the parasite and thus the initiation of infection in the human host.

  DOI：

  10.1021/ml500516r

文献信息

• Exploiting the Polypharmacology of ß-Carbolines to Disrupt <i>O. volvulus</i> Molting
  作者：Major Gooyit、Nancy Tricoche、Sacha Javor、Sara Lustigman、Kim D. Janda

  DOI：10.1021/ml500516r

  日期：2015.3.12

  Onchocerciasis is an infection caused by the filarial worm Onchocerca volvulus, which can eventually result in blindness. The lack of an effective macrofilaricide and the possible development of ivermectin-resistant strains of O. volvulus necessitate the, need for alternative treatment strategies. We have shown that targeting the L3-stagespecific chitinase OvCHT1 impairs the shedding of the filarial cuticle. In our continued efforts to discover OvCHT1 inhibitors, we identified the beta-carboline alkaloid scaffolding as a chitinase inhibitor that is capable of penetrating the worm cuticle. Herein, we disclose the rich polypharmacology of the beta-carboline class of compounds as an approach to abrogate the molting of the parasite and thus the initiation of infection in the human host.