2,4-Difluorophenylglucuronide | 147299-91-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,4-Difluorophenylglucuronide
• 英文别名: 2,4-Difluorophenol glucuronide；beta-D-Glucopyranosiduronic acid, 2,4-difluorophenyl；(2S,3S,4S,5R,6S)-6-(2,4-difluorophenoxy)-3,4,5-trihydroxyoxane-2-carboxylic acid
• CAS: 147299-91-0
• 化学式: C₁₂H₁₂F₂O₇
• 分子量: 306.22
• InChiKey: XLYNZFQNIXTJDF-GOVZDWNOSA-N

物化性质

• 沸点：
  558.7±50.0 °C(Predicted)
• 密度：
  1.714±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  116
• 氢给体数：
  4
• 氢受体数：
  9

反应信息

• 作为产物：
  描述：

  2,4-二氟苯酚 、 6-[[[5-(2,4-二氧代嘧啶-1-基)-3,4-二羟基四氢呋喃-2-基]甲氧基-羟基磷酰]氧基-羟基磷酰]氧基-3,4,5-三羟基四氢吡喃-2-羧酸 在 microsomal protein 作用下， 以 phosphate buffer 为溶剂， 生成 2,4-Difluorophenylglucuronide
  参考文献：
  名称：

  Influence of the type of halogen substituent onin vivoandin vitrophase II metabolism of 2-fluoro-4-halophenol metabolites formed from 3-halo-fluorobenzenes

  摘要：

  1. The influence of a change in the type of halogen substituent on phase II metabolism of 2-fluoro-4-halophenol metabolites formed from 3-halo-fluorobenzenes was studied in vivo and in vitro using F-19 nmr and spectroscopic assays.2. The ratio of sulphation to glucuronidation of 2-fluoro-4-halophenol metabolites formed from 3-halofluorobenzenes decreased from 48 to 13 to 6 when the halogen substituent varied from fluorine to chlorine to bromine.3. When the 2-fluoro-4-halophenols themselves were administered to the rats, the ratio of sulphation to glucuronidation was not affected by the type of halogen substituent at C4 and at a constant value of 0.6, i.e. significantly lower.4. Kinetic data for P450 catalysed hydroxylation of the 3-halo-fluorobenzenes and for sulphation and glucuronidation of their 2-fluoro-4-halophenol metabolites were obtained from in vitro microsomal and cytosolic incubations. These data demonstrate that the effects of varying the halogen substituent on phase II metabolism of the 2-fluoro-4-halophenol metabolites can be mainly ascribed to an apparently decreased K-m for the glucuronidation of the 2-fluoro-4-halophenols with a change in the halo substituent from fluorine to chlorine to bromine.5. Results from calculations on electronic and structural characteristics of the three 4-halo-2-fluorophenols demonstrate that the best explanation for the decrease in the apparent K-m of the glucuronidation from 2,4-difluoro- to 4-chloro-2-fluoro- to 4-bromo-2-fluorophenol might be an increase in the hydrophobicity of the phenol. An increase in the hydrophobicity of the phenol would provide an increased possibility for substrate accumulation in the hydrophobic membrane environment of the UDP-glucuronyltransferases, resulting in an apparently decreased K-m.

  DOI：

  10.3109/00498259409043276