4-(5-(1H-imidazol-1-yl)-3-methyl-1-phenyl-1H-pyrazol-4-yl)-2-amino-6-(2,2-dimethylbenzo[d][1,3]dioxol-5-yl)nicotinonitrile | 1620514-43-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 4-(5-(1H-imidazol-1-yl)-3-methyl-1-phenyl-1H-pyrazol-4-yl)-2-amino-6-(2,2-dimethylbenzo[d][1,3]dioxol-5-yl)nicotinonitrile
• 英文别名: 2-Amino-6-(2,2-dimethyl-1,3-benzodioxol-5-yl)-4-(5-imidazol-1-yl-3-methyl-1-phenylpyrazol-4-yl)pyridine-3-carbonitrile；2-amino-6-(2,2-dimethyl-1,3-benzodioxol-5-yl)-4-(5-imidazol-1-yl-3-methyl-1-phenylpyrazol-4-yl)pyridine-3-carbonitrile
• CAS: 1620514-43-3
• 化学式: C₂₈H₂₃N₇O₂
• 分子量: 489.536
• InChiKey: MVTVBWUKVRTDLM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  37
• 可旋转键数：
  4
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  117
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  5-氯-3-甲基-1-苯基吡唑-4-甲醛 在 ammonium acetate 、 potassium carbonate 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 2.75h， 生成 4-(5-(1H-imidazol-1-yl)-3-methyl-1-phenyl-1H-pyrazol-4-yl)-2-amino-6-(2,2-dimethylbenzo[d][1,3]dioxol-5-yl)nicotinonitrile
  参考文献：
  名称：

  Ultrasound-assisted one-pot four-component synthesis of novel 2-amino-3-cyanopyridine derivatives bearing 5-imidazopyrazole scaffold and their biological broadcast

  摘要：

  An alternative and environmentally caring way for the synthesis of novel 2-amino-3-cyanopyridine derivatives bearing 5-imidazopyrazole nucleus is reported by one-pot four-component cyclocondensation reaction of substituted 5-(1H-imidazol/4-methyl-1-yl)-3-methyl-1-phenyl-1H-pyrazole-4-carbaldehyde (3a-b), malononitrile (4), ammonium acetate (5) and aromatic (6a-f)/heterocyclic methyl ketones (7a-d) under ultrasonic irradiation. The newly synthesized compounds were evaluated for their in vitro antibacterial activity against a panel of pathogenic stains of bacteria and fungi, in vitro antitubercular activity against Mycobacterium tuberculosis H37Rv stain and in vitro antioxidant activity by ferric-reducing antioxidant power method. Compounds 8e, 8h, 8l, 9c, 9g and 9h exhibited excellent antibacterial activity and compounds 3a, 8k, 9a and 9bshowed moderate antituberculosis activity as compared with the first line drugs. Majority of the compounds showed excellent antioxidant activity. This approaches claimed to be an environment friendly protocol as it afforded numerous advantages i.e. excellent yields, cleaner reaction profile and shorter reaction time.

  DOI：

  10.1016/j.ejmech.2014.06.071