4-{[3-chloro-6-(3-furanyl)-8-(trifluoromethyl)imidazo[1,2-a]pyridin-2-yl]carbonyl}-1-phenyl-2-piperazinone | 1284243-09-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪烷类
• 英文名称: 4-{[3-chloro-6-(3-furanyl)-8-(trifluoromethyl)imidazo[1,2-a]pyridin-2-yl]carbonyl}-1-phenyl-2-piperazinone
• 英文别名: 4-[3-Chloro-6-(furan-3-yl)-8-(trifluoromethyl)imidazo[1,2-a]pyridine-2-carbonyl]-1-phenylpiperazin-2-one
• CAS: 1284243-09-9
• 化学式: C₂₃H₁₆ClF₃N₄O₃
• 分子量: 488.853
• InChiKey: JKVXQTUZMGYBOQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  34
• 可旋转键数：
  3
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  71.1
• 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 4-{[3-chloro-6-(3-furanyl)-8-(trifluoromethyl)imidazo[1,2-a]pyridin-2-yl]carbonyl}-1-phenyl-2-piperazinone
  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

• [EN] PIPERAZINYL ANTIVIRAL AGENTS<br/>[FR] AGENTS ANTI-VIRAUX À BASE DE PIPÉRAZINYLE
  申请人：GLAXOSMITHKLINE LLC

  公开号：WO2011041713A3

  公开（公告）日：2012-04-05
• 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.