4-amino-1-methyl-N-(2-morpholinoethyl)-1H-imidazole-2-carboxamide | 1211528-91-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 恶嗪烷类
• 英文名称: 4-amino-1-methyl-N-(2-morpholinoethyl)-1H-imidazole-2-carboxamide
• CAS: 1211528-91-4
• 化学式: C₁₁H₁₉N₅O₂
• 分子量: 253.304
• InChiKey: YCDQTSRCGSDLDQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.94
• 重原子数：
  18.0
• 可旋转键数：
  4.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  85.41
• 氢给体数：
  2.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  4-amino-1-methyl-N-(2-morpholinoethyl)-1H-imidazole-2-carboxamide 、 二苯甲酮-4,4'-二甲酸 在 O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate 、 N,N-二异丙基乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 1-methyl-4-[[4-[4-[[1-methyl-2-(2-morpholin-4-ylethylcarbamoyl)imidazol-4-yl]carbamoyl]benzoyl]benzoyl]amino]-N-(2-morpholin-4-ylethyl)imidazole-2-carboxamide
  参考文献：
  名称：

  Design, Synthesis, and Structure−Activity Relationships of Benzophenone-Based Tetraamides as Novel Antibacterial Agents

  摘要：

  The increase in the incidence of both hospital- and community-acquired antibiotic-resistant infections is a major concern to the healthcare community. There have been only two new classes of antibiotics approved by the FDA over the past 40 years, and clearly there is a growing need For additional antimicrobial agents. In this paper, we present Our work on the discovery of a class of benzophenone containing compounds that possess good activity against MRSA, VISA, VRSA, and VRE and moderate activity against E. coli. These compounds display MIC values in the 0.5-2.0 mg/L range and are not cytotoxic against mammalian cells. Extensive structure-activity relationship studies revealed that the benzophenone was absolutely essential for antibacterial activity as was the presence of a cationic group. Although these agents display DNA binding activity, we observed that these compounds do not inhibit any macromolecular synthesis reliant upon DNA nor do they inhibit lipid or cell wall biosynthesis. Instead, we found that these agents cause membrane depolarization, indicating that the bacterial membrane was the primary site of action for these agents. Our studies Suggest that caution should be taken ill assigning the mechanism of action for DNA binding antibiotics.

  DOI：

  10.1021/jm900519b
• 作为产物：
  描述：

  1-methyl-4-nitro-N-(2-(morpholin-4-yl)ethyl)-1H-imidazole-2-carboxamide 在 palladium 10% on activated carbon 、 氢气 作用下， 以 甲醇 为溶剂， 反应 1.5h， 生成 4-amino-1-methyl-N-(2-morpholinoethyl)-1H-imidazole-2-carboxamide
  参考文献：
  名称：

  Design, Synthesis, and Structure−Activity Relationships of Benzophenone-Based Tetraamides as Novel Antibacterial Agents

  摘要：

  The increase in the incidence of both hospital- and community-acquired antibiotic-resistant infections is a major concern to the healthcare community. There have been only two new classes of antibiotics approved by the FDA over the past 40 years, and clearly there is a growing need For additional antimicrobial agents. In this paper, we present Our work on the discovery of a class of benzophenone containing compounds that possess good activity against MRSA, VISA, VRSA, and VRE and moderate activity against E. coli. These compounds display MIC values in the 0.5-2.0 mg/L range and are not cytotoxic against mammalian cells. Extensive structure-activity relationship studies revealed that the benzophenone was absolutely essential for antibacterial activity as was the presence of a cationic group. Although these agents display DNA binding activity, we observed that these compounds do not inhibit any macromolecular synthesis reliant upon DNA nor do they inhibit lipid or cell wall biosynthesis. Instead, we found that these agents cause membrane depolarization, indicating that the bacterial membrane was the primary site of action for these agents. Our studies Suggest that caution should be taken ill assigning the mechanism of action for DNA binding antibiotics.

  DOI：

  10.1021/jm900519b