4-(3-(4-fluorophenyl)quinoxalin-2-yl)-N-(3-methylbutan-2-yl)pyridin-2-amine | 1207531-79-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 英文名称: 4-(3-(4-fluorophenyl)quinoxalin-2-yl)-N-(3-methylbutan-2-yl)pyridin-2-amine
• 英文别名: 4-[3-(4-fluorophenyl)quinoxalin-2-yl]-N-(3-methylbutan-2-yl)pyridin-2-amine
• CAS: 1207531-79-0
• 化学式: C₂₄H₂₃FN₄
• 分子量: 386.472
• InChiKey: KQRFHCIRRCQGSO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  29
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  50.7
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  2-(4-fluorophenyl)-3-(2-fluoropyridin-4-yl)quinoxaline 、 1,2-甲基丙胺 反应 15.0h， 以97%的产率得到4-(3-(4-fluorophenyl)quinoxalin-2-yl)-N-(3-methylbutan-2-yl)pyridin-2-amine
  参考文献：
  名称：

  Pyridinylquinoxalines and Pyridinylpyridopyrazines as Lead Compounds for Novel p38α Mitogen-Activated Protein Kinase Inhibitors

  摘要：

  Various substituted 2(3)-(4-fluorophenyl)-3(2)-(pyridin-4-yl)quinoxatines and 2(3)-(4-fluorophenyl)3(2)-(pyridin-4-yl)pyridopyrazines were synthesized as novel p38 alpha MAP kinase inhibitors via different short synthetic strategies with high variation possibilities. The formation of the quinoxaline/pyridopyrazine core was achieved from alpha-cliketones and o-phenylenodiamines/alpha-diaminopyridines under microwave irradiation. Introduction of an amino moiety at the pyridine C2 position of the 2(3)-(4-fluorophenyl)-3(2)-(pyridin-4-yl)quinoxalines led to compounds showing potent enzyme inhibition down to the double-digit nanomolar range (6f; IC50 = 81 nM). Replacement of the quinoxaline core with pyrido[2,3-b]pyrazine gave compound 9e with superior p38 alpha MAP kinase inhibition (IC50 = 38 nM).

  DOI：

  10.1021/jm901392x

文献信息

• Pyridinylquinoxalines and Pyridinylpyridopyrazines as Lead Compounds for Novel p38α Mitogen-Activated Protein Kinase Inhibitors
  作者：Pierre Koch、Hartmut Jahns、Verena Schattel、Marcia Goettert、Stefan Laufer

  DOI：10.1021/jm901392x

  日期：2010.2.11

  Various substituted 2(3)-(4-fluorophenyl)-3(2)-(pyridin-4-yl)quinoxatines and 2(3)-(4-fluorophenyl)3(2)-(pyridin-4-yl)pyridopyrazines were synthesized as novel p38 alpha MAP kinase inhibitors via different short synthetic strategies with high variation possibilities. The formation of the quinoxaline/pyridopyrazine core was achieved from alpha-cliketones and o-phenylenodiamines/alpha-diaminopyridines under microwave irradiation. Introduction of an amino moiety at the pyridine C2 position of the 2(3)-(4-fluorophenyl)-3(2)-(pyridin-4-yl)quinoxalines led to compounds showing potent enzyme inhibition down to the double-digit nanomolar range (6f; IC50 = 81 nM). Replacement of the quinoxaline core with pyrido[2,3-b]pyrazine gave compound 9e with superior p38 alpha MAP kinase inhibition (IC50 = 38 nM).