9H-pyrido[3,4-b]indole-6-sulfonyl chloride | 1309919-38-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: 9H-pyrido[3,4-b]indole-6-sulfonyl chloride
• CAS: 1309919-38-7
• 化学式: C₁₁H₇ClN₂O₂S
• 分子量: 266.708
• InChiKey: OQIFFHREYYAXKD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  71.2
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  9H-pyrido[3,4-b]indole-6-sulfonyl chloride 在 ammonium hydroxide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 以80%的产率得到9H-pyrido[3,4-b]indole-6-sulfonamide
  参考文献：
  名称：

  Design, synthesis and biological evaluation of β-carboline derivatives as novel inhibitors targeting B-Raf kinase

  摘要：

  beta-Carboline family of compounds is a large group of alkaloids widely distributed in nature and exhibits broad-spectrum anti-tumor activities. We designed and synthesized two series of novel 1-carboxamide- and 6-sulfonamide-substituted beta-carboline derivatives 7a-p and 12a-b, and their wild type B-Raf kinase inhibitory activities were described. Most compounds showed moderate to excellent inhibitory activities. Among them, 1-carboxamide-6-(N-(3-(dimethylamino)propyl)-sulfamoyl)-beta-carboline, 7e exhibited potent activity (IC50 = 1.62 mu M), showing the potential for further investigation as a lead compound. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.05.053
• 作为产物：
  描述：

  (S)-2,3,4,9-四氢-1H-吡啶[3,4-b]吲哚-3-羧酸 在 氯磺酸 、 selenium(IV) oxide 、 溶剂黄146 作用下， 反应 12.0h， 生成 9H-pyrido[3,4-b]indole-6-sulfonyl chloride
  参考文献：
  名称：

  Design, synthesis and biological evaluation of β-carboline derivatives as novel inhibitors targeting B-Raf kinase

  摘要：

  beta-Carboline family of compounds is a large group of alkaloids widely distributed in nature and exhibits broad-spectrum anti-tumor activities. We designed and synthesized two series of novel 1-carboxamide- and 6-sulfonamide-substituted beta-carboline derivatives 7a-p and 12a-b, and their wild type B-Raf kinase inhibitory activities were described. Most compounds showed moderate to excellent inhibitory activities. Among them, 1-carboxamide-6-(N-(3-(dimethylamino)propyl)-sulfamoyl)-beta-carboline, 7e exhibited potent activity (IC50 = 1.62 mu M), showing the potential for further investigation as a lead compound. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.05.053

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.