N-butyl-2-[2-(4-fluorophenyl)-4-methyl-3-oxo-2H-pyrazolo[ 3,4-b]-quinolin-9(3H)-yl]-N-methylacetamide | 1337537-61-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: N-butyl-2-[2-(4-fluorophenyl)-4-methyl-3-oxo-2H-pyrazolo[ 3,4-b]-quinolin-9(3H)-yl]-N-methylacetamide
• 英文别名: N-butyl-2-[2-(4-fluorophenyl)-4-methyl-3-oxopyrazolo[3,4-b]quinolin-9-yl]-N-methylacetamide
• CAS: 1337537-61-7
• 化学式: C₂₄H₂₅FN₄O₂
• 分子量: 420.487
• InChiKey: XMSNXDPXGVQOSR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  31
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  56.2
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  甲基丁胺 在 sodium carbonate 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 生成 N-butyl-2-[2-(4-fluorophenyl)-4-methyl-3-oxo-2,3-dihydro-1H-pyrazolo[3,4-b]quinolin-1-yl]-N-methylacetamide 、 N-butyl-2-[2-(4-fluorophenyl)-4-methyl-3-oxo-2H-pyrazolo[ 3,4-b]-quinolin-9(3H)-yl]-N-methylacetamide
  参考文献：
  名称：

  Synthesis and Structure–Activity Relationship Studies in Translocator Protein Ligands Based on a Pyrazolo[3,4-b]quinoline Scaffold

  摘要：

  As a further development of our large program focused on the medicinal chemistry of translocator protein [TSPO (18 kDa)] ligands, a new class of compounds related to alpidem has been designed using SSR180575, emapunil, and previously published pyrrolo[3,4-b]quinoline derivatives 9 as templates. The designed compounds were synthesized by alkylation of the easily accessible 4-methyl-2-phenyl-1H-pyrazolo[3,4-b]quinolin-3(2H)-one derivatives 13-15 with the required bromoacetamides. Along with the expected 2-(4-methyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazolo[3,4-b]quinolin-1-yl)acetamide derivatives 10, 2-(4-methyl-3-oxo-2-phenyl-2H-pyrazolo[3,4-b]quinolin-9(3H)-yl)acetamide isomers 11 were isolated and characterized. The high TSPO affinity shown by new pyrazolo[3,4-b]quinoline derivatives 10 and especially 11 leads the way to further expand the chemical diversity in TSPO ligands and provides new templates and structure affinity relationship data potentially useful in the design of new anxiolytic and neuroprotective agents.

  DOI：

  10.1021/jm200770f