3-acryloyloxy-4-(2-chlorophenyl)azetidin-2-one | 923588-06-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酰胺类
• 英文名称: 3-acryloyloxy-4-(2-chlorophenyl)azetidin-2-one
• 英文别名: 2-(2-Chlorophenyl)-4-oxoazetidin-3-yl prop-2-enoate；[2-(2-chlorophenyl)-4-oxoazetidin-3-yl] prop-2-enoate
• CAS: 923588-06-1
• 化学式: C₁₂H₁₀ClNO₃
• 分子量: 251.669
• InChiKey: GXSHJJJHTMDPDP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  55.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-acryloyloxy-4-(2-chlorophenyl)azetidin-2-one 、 N-(乙基硫代)邻苯二甲酰亚胺 在 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 以82%的产率得到Acrylic acid 2-(2-chloro-phenyl)-1-methylsulfanyl-4-oxo-azetidin-3-yl ester
  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：

  3-acryloyloxy-4-(2-chlorophenyl)-N-(4-methoxyphenyl)azetidin-2-one 在 ammonium cerium(IV) nitrate 作用下， 以 乙腈 为溶剂， 反应 0.67h， 以90%的产率得到3-acryloyloxy-4-(2-chlorophenyl)azetidin-2-one
  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

文献信息

• Antibiotic-conjugated polyacrylate nanoparticles: New opportunities for development of anti-MRSA agents
  作者：Edward Turos、Jeung-Yeop Shim、Yang Wang、Kerriann Greenhalgh、G. Suresh Kumar Reddy、Sonja Dickey、Daniel V. Lim

  DOI：10.1016/j.bmcl.2006.09.098

  日期：2007.1

  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.