5-Bromo-4-chloro-1-(phenylsulfonyl)-1H-pyrrolo[2,3-B]pyridine-2-carboxylic acid | 1394122-99-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 5-Bromo-4-chloro-1-(phenylsulfonyl)-1H-pyrrolo[2,3-B]pyridine-2-carboxylic acid
• 英文别名: 1-(benzenesulfonyl)-5-bromo-4-chloropyrrolo[2,3-b]pyridine-2-carboxylic acid
• CAS: 1394122-99-6
• 化学式: C₁₄H₈BrClN₂O₄S
• 分子量: 415.652
• InChiKey: TXOGLBISEITLHN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  97.6
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  5-Bromo-4-chloro-1-(phenylsulfonyl)-1H-pyrrolo[2,3-B]pyridine-2-carboxylic acid 在 potassium carbonate 、 N,N-二异丙基乙胺 、 Methanaminium,N-[(dimethylamino)(3H-1,2,3-triazolo[4,5-b]pyridin-3-yloxy)methylene]-N-methyl-, hexafluorophosphate(1-) 作用下， 以 N-甲基吡咯烷酮 、 N,N-二甲基甲酰胺 为溶剂， 生成 5-bromo-N-propan-2-yl-4-[3-(trifluoromethyl)pyrazol-1-yl]-1H-pyrrolo[2,3-b]pyridine-2-carboxamide
  参考文献：
  名称：

  Discovery of a novel azaindole class of antibacterial agents targeting the ATPase domains of DNA gyrase and Topoisomerase IV

  摘要：

  We present the discovery and optimization of a novel series of bacterial topoisomerase inhibitors. Starting from a virtual screening hit, activity was optimized through a combination of structure-based design and physical property optimization. Synthesis of fewer than a dozen compounds was required to achieve inhibition of the growth of methicillin-resistant Staphyloccus aureus (MRSA) at compound concentrations of 1.56 mu M. These compounds simultaneously inhibit DNA gyrase and Topoisomerase IV at similar nanomolar concentrations, reducing the likelihood of the spontaneous occurrence of target-based mutations resulting in antibiotic resistance, an increasing threat in the treatment of serious infections. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.05.128
• 作为产物：
  描述：

  5-溴-4-氯-1-(三异丙基硅烷基)-7-氮杂吲哚 在 硫酸 、 sodium hydride 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 异丙醇 为溶剂， 生成 5-Bromo-4-chloro-1-(phenylsulfonyl)-1H-pyrrolo[2,3-B]pyridine-2-carboxylic acid
  参考文献：
  名称：

  Discovery of a novel azaindole class of antibacterial agents targeting the ATPase domains of DNA gyrase and Topoisomerase IV

  摘要：

  We present the discovery and optimization of a novel series of bacterial topoisomerase inhibitors. Starting from a virtual screening hit, activity was optimized through a combination of structure-based design and physical property optimization. Synthesis of fewer than a dozen compounds was required to achieve inhibition of the growth of methicillin-resistant Staphyloccus aureus (MRSA) at compound concentrations of 1.56 mu M. These compounds simultaneously inhibit DNA gyrase and Topoisomerase IV at similar nanomolar concentrations, reducing the likelihood of the spontaneous occurrence of target-based mutations resulting in antibiotic resistance, an increasing threat in the treatment of serious infections. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.05.128