ethyl 5-(2-(1-methyl-4-phenyl-1H-imidazol-2-yl)ethyl)pyrazolo[5,1-f][1,6]naphthyridine-2-carboxylate | 1621622-60-3

• 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: ethyl 5-(2-(1-methyl-4-phenyl-1H-imidazol-2-yl)ethyl)pyrazolo[5,1-f][1,6]naphthyridine-2-carboxylate
• 英文别名: Ethyl 5-[2-(1-methyl-4-phenylimidazol-2-yl)ethyl]pyrazolo[5,1-f][1,6]naphthyridine-2-carboxylate；ethyl 5-[2-(1-methyl-4-phenylimidazol-2-yl)ethyl]pyrazolo[5,1-f][1,6]naphthyridine-2-carboxylate
• CAS: 1621622-60-3
• 化学式: C₂₅H₂₃N₅O₂
• 分子量: 425.49
• InChiKey: HRNULPRQCFJBRP-UHFFFAOYSA-N

物化性质

• 熔点：
  172-174 °C
• 密度：
  1.28±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  32
• 可旋转键数：
  7
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  74.3
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  ethyl 5-(2-(1-methyl-4-phenyl-1H-imidazol-2-yl)ethyl)pyrazolo[5,1-f][1,6]naphthyridine-2-carboxylate 在 sodium tetrahydroborate 、 sodium hydride 作用下， 以 四氢呋喃 、 乙醇 、 mineral oil 为溶剂， 反应 24.5h， 生成 2-(methoxymethyl)-5-(2-(1-methyl-4-phenyl-1H-imidazol-2-yl)ethyl)pyrazolo[5,1-f][1,6]naphthyridine
  参考文献：
  名称：

  Synthesis and SAR study of novel tricyclic pyrazoles as potent phosphodiesterase 10A inhibitors

  摘要：

  Novel pyrazolo[5,1-f][1,6]naphthyridines, pyrazolo[5,1-a][2,6]naphthyridines, pyrazolo[5,1-a][2,7]naphthyridines and pyrazolo[5,1-a]isoquinolines phenylimidazole/benzimidazole ethylene-linked were designed and synthesized for PDE10A interaction. An AgOTf and proline-cocatalyzed multicomponent methodology based on use of o-alkynylaldehydes, tosylhydrazide and ketones was developed and proved to be a convenient route for assembly of most of the novel tricyclic pyrazoles synthesized. Pyrazolo[5,1-f][1,6]naphthyridine 43 and 59, pyrazolo[5,1-a][2,6]naphthyridine 66, and pyrazolo[5,1-a][2,7]naphthyridine 42 showed the highest affinity for PDE10A enzyme (IC50 = 40, 42, 40, 55 nM, respectively).

  DOI：

  10.1016/j.ejmech.2014.07.020
• 作为产物：
  描述：

  2-溴-3-吡啶甲醛 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 氯化亚砜 、 silver trifluoromethanesulfonate 、 三溴化硼 、 sodium hydride 、 sodium carbonate 、 对甲苯磺酸 、 三乙胺 、 DL-脯氨酸 作用下， 以 乙醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 乙腈 、 mineral oil 为溶剂， 反应 43.83h， 生成 ethyl 5-(2-(1-methyl-4-phenyl-1H-imidazol-2-yl)ethyl)pyrazolo[5,1-f][1,6]naphthyridine-2-carboxylate
  参考文献：
  名称：

  Synthesis and SAR study of novel tricyclic pyrazoles as potent phosphodiesterase 10A inhibitors

  摘要：

  Novel pyrazolo[5,1-f][1,6]naphthyridines, pyrazolo[5,1-a][2,6]naphthyridines, pyrazolo[5,1-a][2,7]naphthyridines and pyrazolo[5,1-a]isoquinolines phenylimidazole/benzimidazole ethylene-linked were designed and synthesized for PDE10A interaction. An AgOTf and proline-cocatalyzed multicomponent methodology based on use of o-alkynylaldehydes, tosylhydrazide and ketones was developed and proved to be a convenient route for assembly of most of the novel tricyclic pyrazoles synthesized. Pyrazolo[5,1-f][1,6]naphthyridine 43 and 59, pyrazolo[5,1-a][2,6]naphthyridine 66, and pyrazolo[5,1-a][2,7]naphthyridine 42 showed the highest affinity for PDE10A enzyme (IC50 = 40, 42, 40, 55 nM, respectively).

  DOI：

  10.1016/j.ejmech.2014.07.020

文献信息

• Synthesis and SAR study of novel tricyclic pyrazoles as potent phosphodiesterase 10A inhibitors
  作者：Antonio Dore、Battistina Asproni、Alessia Scampuddu、Gerard Aime Pinna、Claus Tornby Christoffersen、Morten Langgård、Jan Kehler

  DOI：10.1016/j.ejmech.2014.07.020

  日期：2014.9

  Novel pyrazolo[5,1-f][1,6]naphthyridines, pyrazolo[5,1-a][2,6]naphthyridines, pyrazolo[5,1-a][2,7]naphthyridines and pyrazolo[5,1-a]isoquinolines phenylimidazole/benzimidazole ethylene-linked were designed and synthesized for PDE10A interaction. An AgOTf and proline-cocatalyzed multicomponent methodology based on use of o-alkynylaldehydes, tosylhydrazide and ketones was developed and proved to be a convenient route for assembly of most of the novel tricyclic pyrazoles synthesized. Pyrazolo[5,1-f][1,6]naphthyridine 43 and 59, pyrazolo[5,1-a][2,6]naphthyridine 66, and pyrazolo[5,1-a][2,7]naphthyridine 42 showed the highest affinity for PDE10A enzyme (IC50 = 40, 42, 40, 55 nM, respectively).