S-(+)-methyl 3-(4-hydroxyphenyl)-2-(2-(4-isobutylphenyl)propanamido)propanoate | 1339077-71-2

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: S-(+)-methyl 3-(4-hydroxyphenyl)-2-(2-(4-isobutylphenyl)propanamido)propanoate
• CAS: 1339077-71-2
• 化学式: C₂₃H₂₉NO₄
• 分子量: 383.488
• InChiKey: PBFUNLDKJGAUKZ-KKSFZXQISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.59
• 重原子数：
  28.0
• 可旋转键数：
  8.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  75.63
• 氢给体数：
  2.0
• 氢受体数：
  4.0

反应信息

• 作为产物：
  描述：

  L-酪氨酸 在 氯化亚砜 、 sodium hydroxide 作用下， 以 水 为溶剂， 反应 0.5h， 生成 S-(+)-methyl 3-(4-hydroxyphenyl)-2-(2-(4-isobutylphenyl)propanamido)propanoate
  参考文献：
  名称：

  Synthesis, hydrolysis studies and phamacodynamic profiles of amide prodrugs of dexibuprofen with amino acids

  摘要：

  The present investigation deals with the synthesis of novel prodrugs of dexibuprofen with amino acids with an aim to achieve potent anti-inflammatory activity and less gastrointestinal toxicity. Structures of synthesized compounds were confirmed by spectral and elemental analyses. In vitro hydrolytic studies in simulated intestinal fluid, 80% plasma and rat faecal matter showed satisfactory release of dexibuprofen due to enzymatic cleavage. The synthesized prodrugs were evaluated for anti-inflammatory activity, analgesia, ulcerogenicity and histopathology. The anti-inflammatory activity of dexibuprofen was 43.3% whereas an improved value of 73.4, 77.3, 72.8 and 64.5% was observed for the synthesized prodrugs. The percentage analgesia of the prodrugs increased, whereas a decrease in the mean ulcer index values than dexibuprofen was observed. The histopathological studies revealed less ulceration in the gastric region when treated with prodrugs. Thus, the prodrugs were proved to be better in action as compared with the parent drug.

  DOI：

  10.3109/14756366.2010.548327