N-[cis-3-(4-Nitro-1H-imidazol-1-yl)cyclobutyl]acetamide | 395074-88-1

• 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-[cis-3-(4-Nitro-1H-imidazol-1-yl)cyclobutyl]acetamide
• 英文别名: N-[3-(4-nitroimidazol-1-yl)cyclobutyl]acetamide
• CAS: 395074-88-1
• 化学式: C₉H₁₂N₄O₃
• 分子量: 224.219
• InChiKey: SQWFPTRSLISJGC-UHFFFAOYSA-N

物化性质

• 沸点：
  565.8±43.0 °C(Predicted)
• 密度：
  1.57±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  92.7
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-[cis-3-(4-Nitro-1H-imidazol-1-yl)cyclobutyl]acetamide 在 palladium 10% on activated carbon 、 氢气 作用下， 以 乙酸乙酯 为溶剂， 23.0 ℃ 、344.75 kPa 条件下， 生成 N-[3-(4-aminoimidazol-1-yl)cyclobutyl]acetamide
  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
• 作为产物：
  描述：

  N-(3-Aminocyclobutyl)acetamide 、 1,4-二硝基咪唑 以 甲醇 为溶剂， 生成 N-[cis-3-(4-Nitro-1H-imidazol-1-yl)cyclobutyl]acetamide
  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