3-乙酰氧基-4-(4-乙酰氧基苯基)-N-(4-甲氧基苯基)氮杂环丁烷-2-酮 | 923588-09-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酰胺类
• 中文名称: 3-乙酰氧基-4-(4-乙酰氧基苯基)-N-(4-甲氧基苯基)氮杂环丁烷-2-酮
• 英文名称: 3-acetoxy-4-(4-acetoxyphenyl)-N-(4-methoxyphenyl)azetidin-2-one
• CAS: 923588-09-4
• 化学式: C₂₀H₁₉NO₆
• 分子量: 369.374
• InChiKey: FLEAXXQIEUWFPF-UHFFFAOYSA-N

物化性质

• 熔点：
  143-144 °C(Solv: methanol (67-56-1))
• 沸点：
  587.1±50.0 °C(Predicted)
• 密度：
  1.32±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.64
• 重原子数：
  27.0
• 可旋转键数：
  5.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  82.14
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  3-乙酰氧基-4-(4-乙酰氧基苯基)-N-(4-甲氧基苯基)氮杂环丁烷-2-酮 在 甲醇 、 氢氧化钾 作用下， 以 丙酮 为溶剂， 反应 0.08h， 以92%的产率得到3-羟基-4-(4-羟基苯基)-1-(4-甲氧基苯基)氮杂环丁烷-2-酮
  参考文献：
  名称：

  Antibiotic-conjugated polyacrylate nanoparticles: New opportunities for development of anti-MRSA agents

  摘要：

  This report describes the preparation of polyacrylate nanoparticles in which an N-thiolated beta-lactam antibiotic is covalently conjugated onto the polymer framework. These nanoparticles are formed in water by emulsion polymerization of an acrylated antibiotic pre-dissolved in a liquid acrylate monomer (or mixture of co-monomers) in the presence of sodium dodecyl sulfate as a surfactant and potassium persulfate as a radical initiator. Dynamic light scattering analysis and electron microscopy images of these emulsions show that the nanoparticles are approximately 40 nm in diameter. The emulsions have potent in vitro antibacterial properties against methicillin-resistant Staphylococcus aureus and have improved bioactivity relative to the non-polymerized form of the antibiotic. A unique feature of this methodology is the ability to incorporate water-insoluble drugs directly into the nanoparticle framework without the need for post-synthetic modification. Additionally, the antibiotic properties of the nanoparticles can be modulated by changing the length or location of the acrylate linker on the drug monomer. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.09.098
• 作为产物：
  描述：

  甲氧苯胺 在 (+)-10-camphorsulfonic acid 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 3.25h， 生成 3-乙酰氧基-4-(4-乙酰氧基苯基)-N-(4-甲氧基苯基)氮杂环丁烷-2-酮
  参考文献：
  名称：

  Antibiotic-conjugated polyacrylate nanoparticles: New opportunities for development of anti-MRSA agents

  摘要：

  This report describes the preparation of polyacrylate nanoparticles in which an N-thiolated beta-lactam antibiotic is covalently conjugated onto the polymer framework. These nanoparticles are formed in water by emulsion polymerization of an acrylated antibiotic pre-dissolved in a liquid acrylate monomer (or mixture of co-monomers) in the presence of sodium dodecyl sulfate as a surfactant and potassium persulfate as a radical initiator. Dynamic light scattering analysis and electron microscopy images of these emulsions show that the nanoparticles are approximately 40 nm in diameter. The emulsions have potent in vitro antibacterial properties against methicillin-resistant Staphylococcus aureus and have improved bioactivity relative to the non-polymerized form of the antibiotic. A unique feature of this methodology is the ability to incorporate water-insoluble drugs directly into the nanoparticle framework without the need for post-synthetic modification. Additionally, the antibiotic properties of the nanoparticles can be modulated by changing the length or location of the acrylate linker on the drug monomer. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.09.098