2-(7-methyl-1H-benzo[d]imidazol-2-yl)ethanethioamide | 54980-97-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并咪唑类
• 英文名称: 2-(7-methyl-1H-benzo[d]imidazol-2-yl)ethanethioamide
• 英文别名: 2-(4-methyl-1H-benzimidazol-2-yl)ethanethioamide
• CAS: 54980-97-1
• 化学式: C₁₀H₁₁N₃S
• 分子量: 205.283
• InChiKey: FUZQJXUEPABIIA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  86.8
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-溴戊酸乙酯 、 2-(7-methyl-1H-benzo[d]imidazol-2-yl)ethanethioamide 以 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 以59%的产率得到(E)-2-((7-methyl-1H-benzo[d]imidazol-2-yl)methylene)-5-propylthiazolidin-4-one
  参考文献：
  名称：

  Discovery of a benzimidazole series of ADAMTS-5 (aggrecanase-2) inhibitors by scaffold hopping

  摘要：

  We describe a medicinal chemistry approach to generate a series of benzimidazoles bearing thiazolidin-4-one using scaffold hopping from thiazole 1, our previously described thiazole. Our goal was to discover a potent and permeable small-molecule ADAMTS-5 inhibitor. The results suggest that small compound 22 shows promise as a potent small-molecule ADAMTS-5 inhibitor with good permeability. (C) 2013 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.10.075
• 作为产物：
  描述：

  2,3-二氨基甲苯 在 二硫代磷酸二乙酯 作用下， 以 水 为溶剂， 反应 5.5h， 生成 2-(7-methyl-1H-benzo[d]imidazol-2-yl)ethanethioamide
  参考文献：
  名称：

  Discovery of a benzimidazole series of ADAMTS-5 (aggrecanase-2) inhibitors by scaffold hopping

  摘要：

  We describe a medicinal chemistry approach to generate a series of benzimidazoles bearing thiazolidin-4-one using scaffold hopping from thiazole 1, our previously described thiazole. Our goal was to discover a potent and permeable small-molecule ADAMTS-5 inhibitor. The results suggest that small compound 22 shows promise as a potent small-molecule ADAMTS-5 inhibitor with good permeability. (C) 2013 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.10.075