1-carbamoyl-9H-pyrido[3,4-b]indole-6-sulfonyl chloride | 1309919-37-6

• 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-carbamoyl-9H-pyrido[3,4-b]indole-6-sulfonyl chloride
• CAS: 1309919-37-6
• 化学式: C₁₂H₈ClN₃O₃S
• 分子量: 309.733
• InChiKey: IJUYHNBFVVNFSF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  114
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-carbamoyl-9H-pyrido[3,4-b]indole-6-sulfonyl chloride 在 Ammonium hydroxide 作用下， 生成 1-carbamoyl-6-aminosulfonyl-β-carboline
  参考文献：
  名称：

  Synthesis and Structure of the β-Carboline Derivatives and Their Binding Intensity with Cyclin-Dependent Kinase 2

  摘要：

  一系列3-取代的6-氨基磺酰基-β-咔啉被设计和合成。此外，通过荧光测量和分子对接计算研究了这些β-咔啉衍生物与细胞周期依赖性激酶2（CDK2）的结合模式。结果显示，3-环己基甲氧基团的取代会增加与CDK2深疏水口袋的疏水性结合相互作用，这与更高的结合强度相关。

  DOI：

  10.1248/cpb.60.435
• 作为产物：
  描述：

  ethyl 2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole-1-carboxylate 在 potassium permanganate 、 chlorosulphone 、 氨 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 生成 1-carbamoyl-9H-pyrido[3,4-b]indole-6-sulfonyl chloride
  参考文献：
  名称：

  Synthesis and Structure of the β-Carboline Derivatives and Their Binding Intensity with Cyclin-Dependent Kinase 2

  摘要：

  一系列3-取代的6-氨基磺酰基-β-咔啉被设计和合成。此外，通过荧光测量和分子对接计算研究了这些β-咔啉衍生物与细胞周期依赖性激酶2（CDK2）的结合模式。结果显示，3-环己基甲氧基团的取代会增加与CDK2深疏水口袋的疏水性结合相互作用，这与更高的结合强度相关。

  DOI：

  10.1248/cpb.60.435

文献信息

• Design, synthesis and biological evaluation of β-carboline derivatives as novel inhibitors targeting B-Raf kinase
  作者：Botao Xin、Weifang Tang、Yue Wang、Guowu Lin、Haichun Liu、Yu Jiao、Yong Zhu、Haoliang Yuan、Yadong Chen、Tao Lu

  DOI：10.1016/j.bmcl.2012.05.053

  日期：2012.7

  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.
• Synthesis and Structure of the β-Carboline Derivatives and Their Binding Intensity with Cyclin-Dependent Kinase 2
  作者：Yue Wang、Qiaomei Jin、Guowu Lin、Taotao Yang、Zhanwei Wang、Yi Lu、Yimin Tang、Lifang Liu、Tao Lu

  DOI：10.1248/cpb.60.435

  日期：——

  Series of 3-substituted of 6-aminosulfonyl-β-carbolines were designed and synthesized. In addition, the binding mode of these β-carboline derivatives with cyclin-dependent kinase 2 (CDK2) was studied by means of fluorescence measurements and molecular docking calculation. The results showed that replacement of 3-cyclohexylmethoxy group will increase the hydrophobic binding interaction with the deep hydrophobic pocket of CDK2 correlate to the higher binding intensity.

  一系列3-取代的6-氨基磺酰基-β-咔啉被设计和合成。此外，通过荧光测量和分子对接计算研究了这些β-咔啉衍生物与细胞周期依赖性激酶2（CDK2）的结合模式。结果显示，3-环己基甲氧基团的取代会增加与CDK2深疏水口袋的疏水性结合相互作用，这与更高的结合强度相关。