N-(1-cyclobutylimidazol-4-yl)-2-naphthalen-1-ylacetamide | 1193639-15-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: N-(1-cyclobutylimidazol-4-yl)-2-naphthalen-1-ylacetamide
• CAS: 1193639-15-4
• 化学式: C₁₉H₁₉N₃O
• 分子量: 305.379
• InChiKey: DBDLWYCQSVIKRY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  46.9
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  1-萘乙酸 、 1-cyclobutyl-1H-imidazol-4-amine 在 1-丙基磷酸酐 、 三乙胺 作用下， 以 乙酸乙酯 为溶剂， 生成 N-(1-cyclobutylimidazol-4-yl)-2-naphthalen-1-ylacetamide
  参考文献：
  名称：

  Potent and cellularly active 4-aminoimidazole inhibitors of cyclin-dependent kinase 5/p25 for the treatment of Alzheimer’s disease

  摘要：

  Utilizing structure-based drug design, a 4-aminoimidazole heterocyclic core was synthesized as a replacement for a 2-aminothiazole due to potential metabolically mediated toxicity. The synthetic route utilized allowed for ready synthesis of 1-substituted-4-aminoimidazoles. SAR exploration resulted in the identification of a novel cis-substituted cyclobutyl group that gave improved enzyme and cellular potency against cdk5/p25 with up to 30-fold selectivity over cdk2/cyclin E. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.08.019

文献信息

• Potent and cellularly active 4-aminoimidazole inhibitors of cyclin-dependent kinase 5/p25 for the treatment of Alzheimer’s disease
  作者：Christopher J. Helal、Zhijun Kang、John C. Lucas、Thomas Gant、Michael K. Ahlijanian、Joel B. Schachter、Karl E.G. Richter、James M. Cook、Frank S. Menniti、Kristin Kelly、Scot Mente、Jay Pandit、Natalie Hosea

  DOI：10.1016/j.bmcl.2009.08.019

  日期：2009.10

  Utilizing structure-based drug design, a 4-aminoimidazole heterocyclic core was synthesized as a replacement for a 2-aminothiazole due to potential metabolically mediated toxicity. The synthetic route utilized allowed for ready synthesis of 1-substituted-4-aminoimidazoles. SAR exploration resulted in the identification of a novel cis-substituted cyclobutyl group that gave improved enzyme and cellular potency against cdk5/p25 with up to 30-fold selectivity over cdk2/cyclin E. (C) 2009 Elsevier Ltd. All rights reserved.