4-(1-(3-methoxyphenethyl)-1H-1,2,3-triazol-4-yl)-2-nitroaniline | 1333406-69-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 4-(1-(3-methoxyphenethyl)-1H-1,2,3-triazol-4-yl)-2-nitroaniline
• CAS: 1333406-69-1
• 化学式: C₁₇H₁₇N₅O₃
• 分子量: 339.354
• InChiKey: DMUMICGSMGRELK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.69
• 重原子数：
  25.0
• 可旋转键数：
  6.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  109.1
• 氢给体数：
  1.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  甲酸 、 4-(1-(3-methoxyphenethyl)-1H-1,2,3-triazol-4-yl)-2-nitroaniline 在 palladium on activated charcoal 、 sodium formate 、 原甲酸三乙酯 作用下， 反应 24.0h， 生成 5-(1-(3-methoxyphenethyl)-1H-1,2,3-triazol-4-yl)-1H-benzo[d]imidazole
  参考文献：
  名称：

  Structure–Activity Relationships of Benzimidazole-Based Glutaminyl Cyclase Inhibitors Featuring a Heteroaryl Scaffold

  摘要：

  Glutaminyl cyclase (hQC) has emerged as a new potential target for the treatment of Alzheimer's disease (AD). The inhibition of hQC prevents of the formation of the A beta(3(pE)-40,42) species which were shown to be of elevated neurotoidcity and are likely to act as a seeding core, leading to an accelerated formation of A beta-oligomers and fibrils. This work presents a new class of inhibitors of hQC, resulting from a pharmacophore-based screen. Hit molecules were identified, containing benzimidazole as the metal binding group connected to 1,3,4-oxadiazole as the central scaffold. The subsequent optimization resulted in benzimidazoly1-1,3,4-thiadiazoles and -1,2,3-triazoles with an inhibitory potency in the nanomolar range. Further investigation into the potential binding mode of the new compound classes combined molecular docking and site directed mutagenesis studies.

  DOI：

  10.1021/jm4001709
• 作为产物：
  描述：

  4-碘-2-硝基苯胺 在 甲醇 、 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 sodium azide 、 potassium carbonate 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 二甲基亚砜 为溶剂， 反应 35.0h， 生成 4-(1-(3-methoxyphenethyl)-1H-1,2,3-triazol-4-yl)-2-nitroaniline
  参考文献：
  名称：

  Structure–Activity Relationships of Benzimidazole-Based Glutaminyl Cyclase Inhibitors Featuring a Heteroaryl Scaffold

  摘要：

  Glutaminyl cyclase (hQC) has emerged as a new potential target for the treatment of Alzheimer's disease (AD). The inhibition of hQC prevents of the formation of the A beta(3(pE)-40,42) species which were shown to be of elevated neurotoidcity and are likely to act as a seeding core, leading to an accelerated formation of A beta-oligomers and fibrils. This work presents a new class of inhibitors of hQC, resulting from a pharmacophore-based screen. Hit molecules were identified, containing benzimidazole as the metal binding group connected to 1,3,4-oxadiazole as the central scaffold. The subsequent optimization resulted in benzimidazoly1-1,3,4-thiadiazoles and -1,2,3-triazoles with an inhibitory potency in the nanomolar range. Further investigation into the potential binding mode of the new compound classes combined molecular docking and site directed mutagenesis studies.

  DOI：

  10.1021/jm4001709