2-amino-5-bromo-N-phenylpyridine-3-sulfonamide | 1383992-34-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 2-amino-5-bromo-N-phenylpyridine-3-sulfonamide
• CAS: 1383992-34-4
• 化学式: C₁₁H₁₀BrN₃O₂S
• 分子量: 328.189
• InChiKey: KVKNJGJJPIVPDT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  93.5
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-amino-5-bromo-N-phenylpyridine-3-sulfonamide 在 1,1'-双(二苯膦基)二茂铁二氯化钯(II)二氯甲烷复合物 、 potassium acetate 、 三乙胺 作用下， 以 1,4-二氧六环 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 5.0h， 生成 3-amino-6-(6-amino-5-(N-phenylsulfamoyl)pyridin-3-yl)-N-methylpyrazine-2-carboxamide
  参考文献：
  名称：

  Discovery of a Novel Series of Potent and Orally Bioavailable Phosphoinositide 3-Kinase γ Inhibitors

  摘要：

  The phosphoinositide 3-kinases (PI3Ks) have been linked to an extraordinarily diversified group of cellular functions making these enzymes compelling targets for the treatment of disease. A large body of evidence has linked PI3K gamma to the modulation of autoimmune and inflammatory processes making it an intriguing target for drug discovery. Our high-throughput screening (HTS) campaign revealed two hits that were nominated for further optimization studies. The in vitro activity of the first HTS hit, designated as the sulfonylpiperazine scaffold, was optimized utilizing structure-based design. However, nonoptimal pharmacokinetic properties precluded this series from further studies. An overlay of the X-ray structures of the sulfonylpiperazine scaffold and the second HTS hit within their complexes with PI3K gamma revealed a high degree of overlap. This feature was utilized to design a series of hybrid analogues including advanced leads such as 31 with desirable potency, selectivity, and oral bioavailability.

  DOI：

  10.1021/jm300403a
• 作为产物：
  描述：

  2,3-二氨基-5-溴吡啶 在 吡啶 、 盐酸 、 sodium nitrite 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 3.75h， 生成 2-amino-5-bromo-N-phenylpyridine-3-sulfonamide
  参考文献：
  名称：

  Discovery of a Novel Series of Potent and Orally Bioavailable Phosphoinositide 3-Kinase γ Inhibitors

  摘要：

  The phosphoinositide 3-kinases (PI3Ks) have been linked to an extraordinarily diversified group of cellular functions making these enzymes compelling targets for the treatment of disease. A large body of evidence has linked PI3K gamma to the modulation of autoimmune and inflammatory processes making it an intriguing target for drug discovery. Our high-throughput screening (HTS) campaign revealed two hits that were nominated for further optimization studies. The in vitro activity of the first HTS hit, designated as the sulfonylpiperazine scaffold, was optimized utilizing structure-based design. However, nonoptimal pharmacokinetic properties precluded this series from further studies. An overlay of the X-ray structures of the sulfonylpiperazine scaffold and the second HTS hit within their complexes with PI3K gamma revealed a high degree of overlap. This feature was utilized to design a series of hybrid analogues including advanced leads such as 31 with desirable potency, selectivity, and oral bioavailability.

  DOI：

  10.1021/jm300403a

文献信息

• [EN] QUINAZOLINONE DERIVATIVES AS ANTIVIRAL AGENTS<br/>[FR] DÉRIVÉS DE QUINAZOLINONE EN TANT QU'AGENTS ANTIVIRAUX
  申请人：GLAXOSMITHKLINE LLC

  公开号：WO2012087938A1

  公开（公告）日：2012-06-28

  Provided are compounds and pharmaceutically acceptable salts thereof, their pharmaceutical compositions, their methods of preparation, and their use for treating viral infections mediated by a member of the Flaviviridae family of viruses such as hepatitis C virus (HCV).

  提供了化合物及其药用盐，它们的药物组合物，它们的制备方法，以及它们用于治疗由黄病毒科（Flaviviridae）家族成员介导的病毒感染，如丙型肝炎病毒（HCV）的用途。