cholesteryl (S)-ibuprofenate | 2374288-86-3

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 类固醇和类固醇衍生物
• 英文名称: cholesteryl (S)-ibuprofenate
• 英文别名: Cholest-5-en-3-ol (3I(2))-, 3-[(I+/-S)-I+/--methyl-4-(2-methylpropyl)benzeneacetate]；[(3S,8S,9S,10R,13R,14S,17R)-10,13-dimethyl-17-[(2R)-6-methylheptan-2-yl]-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-yl] (2S)-2-[4-(2-methylpropyl)phenyl]propanoate
• CAS: 2374288-86-3
• 化学式: C₄₀H₆₂O₂
• 分子量: 574.931
• InChiKey: AHZNTDCNXYKGOX-PSOYSMQDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.94
• 重原子数：
  42.0
• 可旋转键数：
  10.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  26.3
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为产物：
  描述：

  胆固醇 、 (S)-(+)-布洛芬 在 4-二甲氨基吡啶 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 以75%的产率得到cholesteryl (S)-ibuprofenate
  参考文献：
  名称：

  In search of safe pain relief: The analgesic and anti-inflammatory activity of phytosteryl ibuprofenates

  摘要：

  beta-Sitosteryl (S)-ibuprofenate (2), stigmasteryl (S)-ibuprofenate (3), ergosteryl (S)-ibuprofenate (4), and cholesteryl (S)-ibuprofenate (5) were prepared in 70-75% yields by Steglich esterification and were characterized by 1D and 2D NMR, as well as by MS. The new esters were evaluated in in vivo pain models of antinociception and anti-inflammation using the writhing, formalin, and carrageenan tests, in mice and rats, and the results were compared with those of (S)-ibuprofen (1). Damage to the gastric mucosa of animals was also assessed. The results indicated that 2-5 have comparable or eventually better activity than 1 at the same mg/kg doses. Since the molecular weight ratio of esters 2-5 to ibuprofen is about 3-1, the amount of truly incorporated ibuprofen was roughly one third to achieve similar effects. This resulted in minimal gastrointestinal damage in the stomach of the animals, in contrast to the large gastric injury caused by (S)-ibuprofen.

  DOI：

  10.1016/j.steroids.2019.05.012