[3-Chloro-6-(furan-3-yl)-8-(trifluoromethyl)imidazo[1,2-a]pyridin-2-yl]-(3-thiophen-2-ylpyrrolidin-1-yl)methanone | 1121054-19-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 咪唑并吡啶类
• 英文名称: [3-Chloro-6-(furan-3-yl)-8-(trifluoromethyl)imidazo[1,2-a]pyridin-2-yl]-(3-thiophen-2-ylpyrrolidin-1-yl)methanone
• CAS: 1121054-19-0
• 化学式: C₂₁H₁₅ClF₃N₃O₂S
• 分子量: 465.883
• InChiKey: ZJGKIXYSVZXPIF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  31
• 可旋转键数：
  3
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  79
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  2-氨基-3-三氟甲基-5-溴吡啶 在 (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride 、 potassium phosphate 、 N-氯代丁二酰亚胺 、 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,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 1.0h， 生成 [3-Chloro-6-(furan-3-yl)-8-(trifluoromethyl)imidazo[1,2-a]pyridin-2-yl]-(3-thiophen-2-ylpyrrolidin-1-yl)methanone
  参考文献：
  名称：

  Imidazo[1,2-a]pyridines That Directly Interact with Hepatitis C NS4B: Initial Preclinical Characterization

  摘要：

  A series of imidazo[1,2-a]pyridines which directly bind to HCV Non-Structural Protein 4B (NS4B) is described. This series demonstrates potent in vitro inhibition of HCV replication (EC50 < 10 nM), direct binding to purified NS4B protein (IC50 < 20 nM), and an HCV resistance pattern associated with NS4B (H94N/R, V105L/M, F98L) that are unique among reported HCV clinical assets, suggestive of the potential for additive or synergistic combination with other small molecule inhibitors of HCV replication.

  DOI：

  10.1021/ml300090x

文献信息

• Certain Nitrogen Containing Bicyclic Chemical Entities For Treating Viral Infections
  申请人：Schmitz Franz Ulrich

  公开号：US20120121540A1

  公开（公告）日：2012-05-17

  Provided are certain chemical entities, pharmaceutical compositions, and methods of treatment of a member of the flaviviradae family of viruses such as hepacivirus (Hepatitis C or HCV).

  提供了某些化学实体、制药组合物和治疗方法，用于治疗黄病毒科的成员，例如丙型肝炎病毒（丙肝或HCV）。
• Certain nitrogen containing bicyclic chemical entities for treating viral infections
  申请人：Schmitz Franz Ulrich

  公开号：US20090176778A1

  公开（公告）日：2009-07-09

  Provided are certain chemical entities, pharmaceutical compositions, and methods of treatment of a member of the flaviviradae family of viruses such as hepacivirus (Hepatitis C or HCV).

  提供了某些化学实体、药物组合物和治疗方法，用于治疗黄病毒科家族成员，如丙型肝炎病毒（Hepatitis C或HCV）。
• NITROGEN CONTAINING BICYCLIC CHEMICAL ENTITIES FOR TREATING VIRAL INFECTIONS
  申请人：GENELABS TECHNOLOGIES, INC.

  公开号：EP2187883A2

  公开（公告）日：2010-05-26
• [EN] CERTAIN NITROGEN CONTAINING BICYCLIC CHEMICAL ENTITIES FOR TREATING VIRAL INFECTIONS<br/>[FR] ENTITÉS CHIMIQUES BICYCLIQUES AZOTÉES POUR TRAITER LES INFECTIONS VIRALES
  申请人：GENELABS TECH INC

  公开号：WO2009023179A2

  公开（公告）日：2009-02-19

  Provided are certain chemical entities selected from compounds of Formula (1) pharmaceutical compositions, and methods of treatment of a member of the flaviviradae family of viruses such as hepacivirus (Hepatitis C or HCV).
• Imidazo[1,2-<i>a</i>]pyridines That Directly Interact with Hepatitis C NS4B: Initial Preclinical Characterization
  作者：J. Brad Shotwell、Subramanian Baskaran、Pek Chong、Katrina L. Creech、Renae M. Crosby、Hamilton Dickson、Jing Fang、Dulce Garrido、Amanda Mathis、Jack Maung、Derek J. Parks、Jeffrey J. Pouliot、Daniel J. Price、Roopa Rai、John W. Seal、Uli Schmitz、Vincent W. F. Tai、Michael Thomson、Mi Xie、Zhiping Z. Xiong、Andrew J. Peat

  DOI：10.1021/ml300090x

  日期：2012.7.12

  A series of imidazo[1,2-a]pyridines which directly bind to HCV Non-Structural Protein 4B (NS4B) is described. This series demonstrates potent in vitro inhibition of HCV replication (EC50 < 10 nM), direct binding to purified NS4B protein (IC50 < 20 nM), and an HCV resistance pattern associated with NS4B (H94N/R, V105L/M, F98L) that are unique among reported HCV clinical assets, suggestive of the potential for additive or synergistic combination with other small molecule inhibitors of HCV replication.