2-(4-isobutylphenyl)-N-(1-adamantyl)propanamide | 405068-77-1

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: 2-(4-isobutylphenyl)-N-(1-adamantyl)propanamide
• 英文别名: N-(1-adamantyl)-2-[4-(2-methylpropyl)phenyl]propanamide
• CAS: 405068-77-1
• 化学式: C₂₃H₃₃NO
• 分子量: 339.521
• InChiKey: LHUBZJBGWIFBBT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6
• 重原子数：
  25
• 可旋转键数：
  5
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  布洛芬 、 金刚烷胺 在 N,N'-二环己基碳二亚胺 作用下， 生成 2-(4-isobutylphenyl)-N-(1-adamantyl)propanamide
  参考文献：
  名称：

  Polycyclic cage structures as carrier molecules for neuroprotective non-steroidal anti-inflammatory drugs

  摘要：

  The blood-brain barrier is formed by the brain capillary endothelium and plays the predominant role in controlling the passage of substances between the blood and the brain. Recent studies on polycyclic structures, i.e. pentacyclo[5.4.0.0(2,6).0(3,10).0(5.9)]undecane and amantadine indicated favourable distribution, thereof to the brain and it was concluded that these polycyclic structures and their derivatives penetrate the blood-brain barrier readily. A series of novel polycyclic prodrugs incorporating the well known nonsteroidal anti-inflammatory drugs (NSAIDs), acetylsalicylic acid and ibuprofen, were synthesised and screened for blood-brain barrier permeability and antioxidant activity. Increased levels of both NSAIDs were detected in the brain tissue of C57BL/6 mice after administration of the synthesised prodrugs, indicating favourable blood-brain barrier permeation. Results from a lipid peroxidation assay indicated that the ester and amide prodrugs significantly increased the ability of the drugs to attenuate lipid peroxidation. These novel prodrugs thus readily penetrate the blood-brain barrier and exhibit increased antioxidant activity when compared to the free NSAIDs. (C) 2009 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2009.01.030