(RS)-ketoprofen vinyl ester | 855519-35-6

• 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: (RS)-ketoprofen vinyl ester
• 英文别名: ketoprofen vinyl ester；Ketoprofen vinyl ester；ethenyl 2-(3-benzoylphenyl)propanoate
• CAS: 855519-35-6
• 化学式: C₁₈H₁₆O₃
• 分子量: 280.323
• InChiKey: UPFGCMKGQFYQGF-UHFFFAOYSA-N

物化性质

• 沸点：
  413.0±38.0 °C(Predicted)
• 密度：
  1.124±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  21
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (RS)-ketoprofen vinyl ester 在 immobilized Lipozyme 作用下， 以 1,4-二氧六环 、 水 为溶剂， 反应 96.0h， 以90%的产率得到(S)-ketoprofen vinyl ester
  参考文献：
  名称：

  Two-step enzymatic selective synthesis of water-soluble ketoprofen–saccharide conjugates in organic media

  摘要：

  Ketoprofen-saccharide conjugates were synthesized by selectively enzymatic hydrolysis and acylation. Firstly, the (S)-ketoprofen vinyl ester was prepared by enzymatic hydrolysis of (R, S)-ketoprofen vinyl ester. Then enzymatic transesterification of (S)-ketoprofen vinyl ester with a series of saccharides were performed by the catalysis of a commercial protease from Bacillus licheniformis (BLP) in organic medium mixture of pyridine and tert-butanol. The ketoprofen was selectively conjugated onto the primary hydroxyl group of saccharides and with high yield after 72 h. Partition coefficient determination showed that all the products have better water solubility than parent ketoprofen. Chemical hydrolysis experiment indicated that 50% ketoprofen could be release from ketoprofen glucoside and maltoside in aqueous buffer (pH 7.4) within 48 h. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2009.01.040
• 作为产物：
  描述：

  乙酸乙烯酯 、 酮基布洛芬 在 mercury(II) diacetate 、 硫酸 作用下， 反应 6.5h， 生成 (RS)-ketoprofen vinyl ester
  参考文献：
  名称：

  Two-step enzymatic selective synthesis of water-soluble ketoprofen–saccharide conjugates in organic media

  摘要：

  Ketoprofen-saccharide conjugates were synthesized by selectively enzymatic hydrolysis and acylation. Firstly, the (S)-ketoprofen vinyl ester was prepared by enzymatic hydrolysis of (R, S)-ketoprofen vinyl ester. Then enzymatic transesterification of (S)-ketoprofen vinyl ester with a series of saccharides were performed by the catalysis of a commercial protease from Bacillus licheniformis (BLP) in organic medium mixture of pyridine and tert-butanol. The ketoprofen was selectively conjugated onto the primary hydroxyl group of saccharides and with high yield after 72 h. Partition coefficient determination showed that all the products have better water solubility than parent ketoprofen. Chemical hydrolysis experiment indicated that 50% ketoprofen could be release from ketoprofen glucoside and maltoside in aqueous buffer (pH 7.4) within 48 h. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2009.01.040

文献信息

• Biocatalytic Synthesis and in Vitro Release of Biodegradable Linear Polyesters with Pendant Ketoprofen
  作者：Hai-Yang Wang、Wei-Wei Zhang、Na Wang、Chao Li、Kun Li、Xiao-Qi Yu

  DOI：10.1021/bm100712k

  日期：2010.12.13

  Enzyme-catalyzed polycondensation for the synthesis of polyester prodrugs of ketoprofen was reported. Lipase acrylic resin from Candida antarctica (CAL-B) was used to synthesize the linear polyesters with pendent ketoprofen groups based on ketoprofen glycerol ester, poly(ethylene glycol), and divinyl sebacate. The products were characterized by GPC and 1H NMR. The results indicated that the molecular

  报道了酶催化缩聚反应合成酮洛芬的聚酯前药。使用来自南极假丝酵母的脂肪酶丙烯酸树脂（CAL-B）合成基于酮洛芬甘油酯，聚乙二醇和癸二酸二乙烯酯的带有侧链酮洛芬基团的线性聚酯。产物通过GPC和1 H NMR表征。结果表明，聚酯的分子量和产率取决于实验条件，例如温度和进料比。体外研究表明，在生理条件下，从聚酯中释放的药物缓慢，这表明聚酯可能是一种有前途的前药，并通过延迟释放酮洛芬而具有扩展的药理作用。
• Two-step enzymatic selective synthesis of water-soluble ketoprofen–saccharide conjugates in organic media
  作者：Hai-Yang Wang、Chao Li、Na Wang、Kun Li、Xing-Wen Feng、Ting He、Xiao-Qi Yu

  DOI：10.1016/j.bmc.2009.01.040

  日期：2009.3

  Ketoprofen-saccharide conjugates were synthesized by selectively enzymatic hydrolysis and acylation. Firstly, the (S)-ketoprofen vinyl ester was prepared by enzymatic hydrolysis of (R, S)-ketoprofen vinyl ester. Then enzymatic transesterification of (S)-ketoprofen vinyl ester with a series of saccharides were performed by the catalysis of a commercial protease from Bacillus licheniformis (BLP) in organic medium mixture of pyridine and tert-butanol. The ketoprofen was selectively conjugated onto the primary hydroxyl group of saccharides and with high yield after 72 h. Partition coefficient determination showed that all the products have better water solubility than parent ketoprofen. Chemical hydrolysis experiment indicated that 50% ketoprofen could be release from ketoprofen glucoside and maltoside in aqueous buffer (pH 7.4) within 48 h. (C) 2009 Elsevier Ltd. All rights reserved.