2-{3-[(E)-(hydroxyimino)(phenyl)methyl]phenyl}propanoic acid

• 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: 2-{3-[(E)-(hydroxyimino)(phenyl)methyl]phenyl}propanoic acid
• 英文别名: 2-[3-[(E)-N-hydroxy-C-phenylcarbonimidoyl]phenyl]propanoic acid
• 化学式: C₁₆H₁₅NO₃
• 分子量: 269.3
• InChiKey: FRONXFGBXAORKI-BMRADRMJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  69.9
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  酮基布洛芬 在 吡啶 、 盐酸羟胺 作用下， 以 1,4-二氧六环 为溶剂， 反应 24.0h， 生成 2-(3-((Hydroxyimino)(phenyl)methyl)phenyl)propanoic acid 、 2-{3-[(E)-(hydroxyimino)(phenyl)methyl]phenyl}propanoic acid
  参考文献：
  名称：

  Evaluation of Hydroxyimine as Cytochrome P450-Selective Prodrug Structure

  摘要：

  Hydroxyimine derivatives of ketoprofen (1) and nabumetone (2) were synthesized and evaluated in vitro and in vivo as cytochrome P450-selective intermediate prodrug structures of ketones. 2 released nabumetone in vitro in the presence of isolated rat and human liver microsomes and in different recombinant human CYP isoforms. Bioconversion of 2 to both nabumetone and its active metabolite, 6-methoxy-2-naphthylacetic acid (6-MNA), was further confirmed in rats in vivo. Results indicate that hydroxyimine is a useful intermediate prodrug structure for ketone drugs.

  DOI：

  10.1021/jm0510124

文献信息

• Evaluation of Hydroxyimine as Cytochrome P450-Selective Prodrug Structure
  作者：Hanna Kumpulainen、Niina Mähönen、Marja-Leena Laitinen、Marja Jaurakkajärvi、Hannu Raunio、Risto O. Juvonen、Jouko Vepsäläinen、Tomi Järvinen、Jarkko Rautio

  DOI：10.1021/jm0510124

  日期：2006.2.1

  Hydroxyimine derivatives of ketoprofen (1) and nabumetone (2) were synthesized and evaluated in vitro and in vivo as cytochrome P450-selective intermediate prodrug structures of ketones. 2 released nabumetone in vitro in the presence of isolated rat and human liver microsomes and in different recombinant human CYP isoforms. Bioconversion of 2 to both nabumetone and its active metabolite, 6-methoxy-2-naphthylacetic acid (6-MNA), was further confirmed in rats in vivo. Results indicate that hydroxyimine is a useful intermediate prodrug structure for ketone drugs.