2-methyl-5-(2-(1-methyl-1H-benzo[d]imidazol-2-yl)ethyl)pyrazolo[5,1-a]isoquinoline | 1621622-67-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异喹啉及其衍生物
• 英文名称: 2-methyl-5-(2-(1-methyl-1H-benzo[d]imidazol-2-yl)ethyl)pyrazolo[5,1-a]isoquinoline
• 英文别名: 2-Methyl-5-[2-(1-methylbenzimidazol-2-yl)ethyl]pyrazolo[5,1-a]isoquinoline；2-methyl-5-[2-(1-methylbenzimidazol-2-yl)ethyl]pyrazolo[5,1-a]isoquinoline
• CAS: 1621622-67-0
• 化学式: C₂₂H₂₀N₄
• 分子量: 340.428
• InChiKey: SSDVSQUNASSUPI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  26
• 可旋转键数：
  3
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  35.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  在 sodium hydride 、 对甲苯磺酸 作用下， 以 N,N-二甲基甲酰胺 、 乙腈 、 mineral oil 为溶剂， 反应 16.5h， 生成 2-methyl-5-(2-(1-methyl-1H-benzo[d]imidazol-2-yl)ethyl)pyrazolo[5,1-a]isoquinoline
  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).