1-methyl-4-nitro-N-(2-(morpholin-4-yl)ethyl)-1H-imidazole-2-carboxamide | 1176170-73-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 1-methyl-4-nitro-N-(2-(morpholin-4-yl)ethyl)-1H-imidazole-2-carboxamide
• 英文别名: 1-methyl-N-(2-morpholin-4-ylethyl)-4-nitroimidazole-2-carboxamide
• CAS: 1176170-73-2
• 化学式: C₁₁H₁₇N₅O₄
• 分子量: 283.287
• InChiKey: SRLQTCJTSOMQBN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.5
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  105
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  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
• 作为产物：
  描述：

  N-(2-氨基乙基)吗啉 、 1-甲基-4-硝基-2-(三氟乙酰)-1H-咪唑 以 N,N-二甲基甲酰胺 为溶剂， 以83%的产率得到1-methyl-4-nitro-N-(2-(morpholin-4-yl)ethyl)-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

文献信息

• Design, Synthesis, and Structure−Activity Relationships of Benzophenone-Based Tetraamides as Novel Antibacterial Agents
  作者：Sunil K. Vooturi、Chrissy M. Cheung、Michael J. Rybak、Steven M. Firestine

  DOI：10.1021/jm900519b

  日期：2009.8.27

  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.