N-(2-benzoyloxypropyl)methacrylamide | 1434118-32-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: N-(2-benzoyloxypropyl)methacrylamide
• 英文别名: 1-(2-Methylprop-2-enoylamino)propan-2-yl benzoate
• CAS: 1434118-32-7
• 化学式: C₁₄H₁₇NO₃
• 分子量: 247.294
• InChiKey: BIGQQZWNAHFPDM-UHFFFAOYSA-N

物化性质

• 沸点：
  431.0±37.0 °C(Predicted)
• 密度：
  1.086±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  18
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.29
• 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：

  N-(2-benzoyloxypropyl)methacrylamide 、 在 偶氮二异丁腈 作用下， 以 N,N-二甲基乙酰胺 为溶剂， 生成
  参考文献：
  名称：

  Biotin-decorated all-HPMA polymeric micelles for paclitaxel delivery

  摘要：

  To avoid poly(ethylene glycol)-related issues of nanomedicines such as accelerated blood clearance, fully N-2-hydroxypropyl methacrylamide (HPMAm)-based polymeric micelles decorated with biotin for drug delivery were designed. To this end, a biotin-functionalized chain transfer agent (CTA), 4-cyano-4-[(dodecylsulfanylthiocarbonyl)-sulfanyl]pentanoic acid (biotin-CDTPA), was synthesized for reversible addition-fragmentation chain-transfer (RAFT) polymerization. Amphiphilic poly(N-2-hydroxypropyl methacrylamide)-block-poly(N-2-benzoyloxypropyl methacrylamide) (p(HPMAm)-b-p(HPMAm-Bz)) with molecular weights ranging from 8 to 24 kDa were synthesized using CDTPA or biotin-CDTPA as CTA and 2,2'-azobis(2-methylpropionitrile) as initiator. The copolymers self-assembled in aqueous media into micelles with sizes of 40-90 nm which positively correlated to the chain length of the hydrophobic block in the polymers, whereas the critical micelle concentrations decreased with increasing hydrophobic block length. The polymer with a molecular weight of 22.1 kDa was used to prepare paclitaxel-loaded micelles which had sizes between 61 and 70 nm, and a maximum loading capacity of around 10 wt%. A549 lung cancer cells overexpressing the biotin receptor, internalized the biotin-decorated micelles more efficiently than non-targeted micelles, while very low internalization of both types of micelles by HEK293 human embryonic kidney cells lacking the biotin receptor was observed. As a consequence, the paclitaxel-loaded micelles with biotin decoration exhibited stronger cytotoxicity in A549 cells than non-targeted micelles. Overall, a synthetic pathway to obtain actively targeted poly(ethylene glycol)-free micelles fully based on a poly(HPMAm) backbone was established. These polymeric micelles are promising systems for the delivery of hydrophobic anticancer drugs.

  DOI：

  10.1016/j.jconrel.2020.09.013
• 作为产物：
  描述：

  N-(2-羟基丙基)甲基丙烯酰胺 、 苯甲酰氯 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 以88%的产率得到N-(2-benzoyloxypropyl)methacrylamide
  参考文献：
  名称：

  Π–Π Stacking Increases the Stability and Loading Capacity of Thermosensitive Polymeric Micelles for Chemotherapeutic Drugs

  摘要：

  Thermosensitive amphiphilic block copolymers self-assemble into micelles above their lower critical solution temperature in water, however, the micelles generally display mediocre physical stability. To stabilize such micelles and increase their loading capacity for chemotherapeutic drugs, block copolymers with novel aromatic monomers were synthesized by free radical polymerization of N-(2-benzoyloxypropyl methacrylamide (HPMAm-Bz) or the corresponding naphthoyl analogue (HPMAm-Nt), with N-(2-hydroxypropyl) methacrylamide monolactate, using a polyethylene glycol based macroinitiator. The critical micelle temperatures and critical micelle concentrations decreased with increasing the HPMAm-Bz/Nt content. The micelles of 30-50 nm were prepared by heating the polymer aqueous solutions from 0 to 50 degrees C and were colloidally stable for at least 48 h at pH 7.4 and 37 degrees C. Paclitaxel and docetaxel encapsulation was performed by mixing drug solutions in ethanol with polymer aqueous solutions and heating from 0 to 50 degrees C. The micelles had a drug loading capacity up to 34 wt % for docetaxel, which is among the highest loadings reported for polymeric micelles, with loaded micelle sizes ranging from 60 to 80 nm. The micelles without aromatic groups almost completely released loaded paclitaxel in 10 days, whereas the HPMAm-Bz/Nt containing micelles released 50% of the paclitaxel at the same time, which showed a better retention for the drug of the latter micelles. H-1 solid-state NMR spectroscopy data are compatible with pi-pi stacking between aromatic groups. The empty micelles demonstrated good cytocompatibility, and paclitaxel-loaded micelles showed high cytotoxicity to tumor cells. In conclusion, the pi-pi stacking effect introduced by aromatic groups increases the stability and loading capacity of polymeric micelles.

  DOI：

  10.1021/bm400234c

文献信息

• POLYMERIC NANOCARRIERS AND METHODS OF USE THEREOF
  申请人：Vanderbilt University

  公开号：US20200323785A1

  公开（公告）日：2020-10-15

  A polymeric nanocarrier and method of treating a bone disease are provided. The polymeric nanocarrier includes an amphiphilic copolymer including a hydrophobic block and a hydrophilic block, where the hydrophilic block comprises a random copolymer. The method of treating a bone disease includes administering the polymeric nanocarrier to a subject in need thereof.