diethyl 7-iodopyrazolo[1,5-a]pyridine-2,3-dicarboxylate | 1385096-50-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡唑并吡啶类
• 英文名称: diethyl 7-iodopyrazolo[1,5-a]pyridine-2,3-dicarboxylate
• CAS: 1385096-50-3
• 化学式: C₁₃H₁₃IN₂O₄
• 分子量: 388.162
• InChiKey: FUZGXXKDRLZEIU-UHFFFAOYSA-N

物化性质

• 密度：
  1.73±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  20
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  69.9
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  氟磺酰基二氟乙酸甲酯 、 diethyl 7-iodopyrazolo[1,5-a]pyridine-2,3-dicarboxylate 在 copper(l) iodide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 以89%的产率得到diethyl 7-(trifluoromethyl)pyrazolo[1,5-a]pyridine-2,3-dicarboxylate
  参考文献：
  名称：

  Synthesis of 7-trifluoromethylpyrazolo[1,5-a]pyridinedicarboxylate

  摘要：

  Two syntheses of 7-trifluoromethylpyrazolo[1,5-a]pyridine dicarboxylate have been described. Approach A utilizes a nucleophilic addition of a trifluoromethyl group to N-p-toluenesulfonyliminopyridinium ylide followed by aromatization and subsequent cycloaddition with diethyl acetylenedicarboxylate to give 1b in modest yield. Approach B involves a selective zincation of pyrazolopyridine dicarboxylate at the C-7 position with (TMP)(2)Zn center dot 2LiCl.2MgCl(2) followed by iodination and trifluoromethylation to give 1b in good yield. The process in approach B has been successfully demonstrated on scale. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2012.09.136
• 作为产物：
  描述：

  吡唑并[1,5-a]吡啶-2,3-二甲酸二乙酯 在 bis(2,2,6,6-tetramethylpiperidinyl)zinc, lithium chloride, magnesium chloride complex 、 碘 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 2.0h， 以85%的产率得到diethyl 7-iodopyrazolo[1,5-a]pyridine-2,3-dicarboxylate
  参考文献：
  名称：

  Hepatitis C Replication Inhibitors That Target the Viral NS4B Protein

  摘要：

  We describe the preclinical development and in vivo efficacy of a novel chemical series that inhibits hepatitis C virus replication via direct interaction with the viral nonstructural protein 4B (NS4B). Significant potency improvements were realized through isosteric modifications to our initial lead la. The temptation to improve antiviral activity while compromising physicochemical properties was tempered by the judicial use of ligand efficiency indices during lead optimization. In this manner, compound la was transformed into (+)-28a which possessed an improved antiviral profile with no increase in molecular weight and only a modest elevation in lipophilicity. Additionally, we employed a chimeric "humanized" mouse model of HCV infection to demonstrate for the first time that a small molecule with high in vitro affinity for NS4B can inhibit viral replication in vivo. This successful proof-of-concept study suggests that drugs targeting NS4B may represent a viable treatment option for curing HCV infection.

  DOI：

  10.1021/jm400125h