ketoprofen vinyl ester

• 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: ketoprofen vinyl ester
• 英文别名: Ethenyl 2-(4-benzoylphenyl)propanoate
• 化学式: C₁₈H₁₆O₃
• 分子量: 280.323
• InChiKey: OXHGKAJEFADHFQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 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：

  ketoprofen vinyl ester 、 β-环糊精 在 Bacillus subtilis alkaline protease 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 72.0h， 以31%的产率得到ketoprofen β-cyclodextrin-mono-2-O-yl ester
  参考文献：
  名称：

  Regioselective synthesis of cyclodextrin mono-substituted conjugates of non-steroidal anti-inflammatory drugs at C-2 secondary hydroxyl by protease in non-aqueous media

  摘要：

  Three P-cyclodextrin (P-CD) conjugates of non-steroidal anti -inflammatory drugs were synthesized by enzymatic methods. Transesterification of P-CD with vinyl ester of indomethacin, ketoprofien and etodolac was performed by the catalysis of alkaline protease from Bacillus subtilis in anhydrous DMF for 3 days. The drug molecules were selectively conjugated onto one of the secondary hydroxyl groups of P-CD through ester-linkage to improve their poor water solubility and absorption characteristics. The products were characterized by ESI-MS, H-1 NMR and C-13 NMR. The structures of products with monoacylation occurring at the C-2 secondary hydroxyl groups of P-CD were confirmed. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2005.03.031

文献信息

• Verfahren zur Herstellung von stereoisomeren Carbonsäureestern
  申请人：BASF AKTIENGESELLSCHAFT

  公开号：EP1031629A2

  公开（公告）日：2000-08-30

  Die vorliegende Erfindung betrifft ein Verfahren zur Herstellung von stereoisomeren Carbonsäureestern bestehend aus einer Säure- und einer Alkohol-Komponente mit jeweils mindestens einem chiralen Zentrum, wobei mindestens ein Stereoisomer des Carbonsäureesters in einem Überschuß vorliegt, indem man einen racemischen Carbonsäureester mit einem racemischen Alkohol in Gegenwart einer Carboxylesterhydrolase (EC 3.1.1) umsetzt.

  本发明涉及一种制备立体异构体羧酸酯的工艺，羧酸酯由一种酸和一种醇组成，每种酸和醇至少有一个手性中心，在羧酸酯水解酶（EC 3.1.1）存在下，外消旋羧酸酯与外消旋醇反应，其中至少有一种羧酸酯的立体异构体过量存在。
• Regioselective synthesis of cyclodextrin mono-substituted conjugates of non-steroidal anti-inflammatory drugs at C-2 secondary hydroxyl by protease in non-aqueous media
  作者：Na Wang、Qi Wu、Yong Mei Xiao、Chun Xiu Chen、Xian Fu Lin

  DOI：10.1016/j.bmc.2005.03.031

  日期：2005.6

  Three P-cyclodextrin (P-CD) conjugates of non-steroidal anti -inflammatory drugs were synthesized by enzymatic methods. Transesterification of P-CD with vinyl ester of indomethacin, ketoprofien and etodolac was performed by the catalysis of alkaline protease from Bacillus subtilis in anhydrous DMF for 3 days. The drug molecules were selectively conjugated onto one of the secondary hydroxyl groups of P-CD through ester-linkage to improve their poor water solubility and absorption characteristics. The products were characterized by ESI-MS, H-1 NMR and C-13 NMR. The structures of products with monoacylation occurring at the C-2 secondary hydroxyl groups of P-CD were confirmed. (c) 2005 Elsevier Ltd. All rights reserved.