4-(2-Chloro-phenyl)-3-hydroxy-1-(4-methoxy-phenyl)-azetidin-2-one | 847201-60-9

• 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: 4-(2-Chloro-phenyl)-3-hydroxy-1-(4-methoxy-phenyl)-azetidin-2-one
• 英文别名: 4-(2-Chlorophenyl)-3-hydroxy-1-(4-methoxyphenyl)azetidin-2-one
• CAS: 847201-60-9
• 化学式: C₁₆H₁₄ClNO₃
• 分子量: 303.745
• InChiKey: VMTANJDSKLCZSR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  49.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-(2-Chloro-phenyl)-3-hydroxy-1-(4-methoxy-phenyl)-azetidin-2-one 在 4-二甲氨基吡啶 、 ammonium cerium(IV) nitrate 、 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 0.08h， 生成 Succinic acid 2-acryloyloxy-ethyl ester 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-Acetoxy-N-(4-methoxyphenyl)-4-(2-chlorophenyl)-2-azetidinone 、 氢氧化钾 、 、 水 以 丙酮 、 甲醇 为溶剂， 反应 0.08h， 以to yield 6.8 g (96%) of 24 as a white solid, mp 178-180° C的产率得到4-(2-Chloro-phenyl)-3-hydroxy-1-(4-methoxy-phenyl)-azetidin-2-one
  参考文献：
  名称：

  Nanoparticles for drug-delivery

  摘要：

  本发明涉及用于药物传递的聚合物纳米粒子，其表面结合有目标分子，其尺寸为最多1000纳米，优选为1纳米至400纳米，更优选为1纳米至200纳米，并在水溶液中均匀分散。目标药物/目标物质与新型聚合物纳米粒子共价结合，以确保它们在体内或体外细胞培养中受到外部干扰，直到它们在细胞内的目标位点暴露出来。本发明还涉及用于制备新型纳米粒子的微乳聚合技术。

  公开号：

  US20070190160A1

文献信息

• US9149440B2
  申请人：——

  公开号：US9149440B2

  公开（公告）日：2015-10-06
• [EN] NANOPARTICLES FOR DRUG-DELIVERY<br/>[FR] NANOPARTICULES POUR APPORT DE MEDICAMENT
  申请人：UNIV SOUTH FLORIDA

  公开号：WO2005020933A2

  公开（公告）日：2005-03-10

  This invention relates to a unique process for the preparation of polymeric nanoparticles with target molecules bonded to the surface of the particles and having sizes of up to 1000nm, preferably Inm to 400nm, more preferably Inm to 200nm, that are dispersed homogeneously in aqueous solution. To accomplish the above objective, the polymeric nanoparticles of the subject invention are prepared using a novel technique of microemulsion polymerization. The resulting aqueous solution of polymeric nanoparticles is comprised of about 1 to 100 parts per weight of water or buffer, about 1 to 80 parts per weight of polymeric nanoparticles, which the bio-active molecules are conjugated, about 0.001 to 10 parts per weight of emulsifier, and about 0.00001 to 5 parts per weight of radical initiator based on the weight of the solution. In the method of this invention, the target drug/target substance is covalently bonded to the polymeric nanoparticles to secure them from outer intervention in vivo or cell culture in vitro until they are exposed at the target site within the cell.
• 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.
• Nanoparticles for drug-delivery
  申请人：Turos Edward

  公开号：US20070190160A1

  公开（公告）日：2007-08-16

  This invention relates to polymeric nanoparticles useful for drug delivery with target molecules bonded to the surface of the particles and having sizes of up to 1000 nm, preferably 1 nm to 400 nm, more preferably 1 nm to 200 nm, that are dispersed homogeneously in aqueous solution. The target drug/target substance is covalently bonded to the novel polymeric nanoparticles to secure them from outer intervention in vivo or cell culture in vitro until they are exposed at the target site within the cell. This invention also relates to microemulsion polymerization techniques useful for preparing the novel nanoparticles.

  本发明涉及用于药物传递的聚合物纳米粒子，其表面结合有目标分子，其尺寸为最多1000纳米，优选为1纳米至400纳米，更优选为1纳米至200纳米，并在水溶液中均匀分散。目标药物/目标物质与新型聚合物纳米粒子共价结合，以确保它们在体内或体外细胞培养中受到外部干扰，直到它们在细胞内的目标位点暴露出来。本发明还涉及用于制备新型纳米粒子的微乳聚合技术。