N-[(S)-4-isobutyl-α-methylphenylacetyl]-L-proline | 662165-78-8

• 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: N-[(S)-4-isobutyl-α-methylphenylacetyl]-L-proline
• 英文别名: (S)-1-((S)-2-(4-isobutylphenyl)propanoyl)pyrrolidine-2-carboxylic acid；(S,S)-1-(2-(4-isobutylphenyl)propanoyl)pyrrolidine-2-carboxylic acid；1-{(2S)-2-[4-(2-Methylpropyl)phenyl]propanoyl}-L-proline；(2S)-1-[(2S)-2-[4-(2-methylpropyl)phenyl]propanoyl]pyrrolidine-2-carboxylic acid
• CAS: 662165-78-8
• 化学式: C₁₈H₂₅NO₃
• 分子量: 303.401
• InChiKey: ZIULIYAPFWDQFO-BBRMVZONSA-N

物化性质

• 熔点：
  112-114 °C
• 沸点：
  497.0±45.0 °C(Predicted)
• 密度：
  1.134±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  57.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  L-半胱氨酸乙酯盐酸盐 、 N-[(S)-4-isobutyl-α-methylphenylacetyl]-L-proline 在 4 A molecular sieve 、 N,N'-羰基二咪唑 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 生成 ethyl (R)-((S)-1-((S)-2-(4-isobutylphenyl)propanoyl)pyrrolidine-2-carbonylamino)-3-mercaptopropanoate
  参考文献：
  名称：

  Design and study of some novel ibuprofen derivatives with potential nootropic and neuroprotective properties

  摘要：

  Six novel ibuprofen derivatives and related structures, incorporating a proline moiety and designed for neurodegenerative disorders, are studied. They possess anti-inflammatory properties and three of them inhibited lipoxygenase. One compound was found to inhibit cyclooxygenase (COX)-2 production in spleenocytes from arthritic rats. The HS-containing compounds are potent antioxidants and one of them protected against glutathione loss after cerebral ischemia/reperfusion. They demonstrated lipid-lowering ability and seem to acquire low gastrointestinal toxicity. Acetylcholinesterase inhibitory activity, found in two of these compounds, may be an asset to their actions. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2006.10.056
• 作为产物：
  描述：

  (S)-(+)-布洛芬 在 草酰氯 、 sodium hydroxide 作用下， 以 二氯甲烷 、 水 为溶剂， 生成 N-[(S)-4-isobutyl-α-methylphenylacetyl]-L-proline
  参考文献：
  名称：

  Compounds against inflammation and oxidative insult as potential agents for neurodegenerative disorders

  摘要：

  Amides of proline, a feature encountered in nootropics, via the carboxylic group of ibuprofen, indomethacin, ketoprofen and naproxen were prepared. Proline carboxylic group was amidated or esterified with potential antioxidant or neuroprotective compounds. Proline was replaced by 4-hydroxyproline, 2-pipecolic acid or omitted, for investigating the contribution of structure to activity. Anti-inflammatory activity was determined, and selected compounds were examined for anti-dyslipidemic action, protection against brain ischaemia/reperfusion and brain penetration.Amides of proline and related structures with NSAIDs were synthesized. They were amidated or esterified with antioxidant or neuroprotective compounds. Activity against lipid peroxidation, inflammation and brain ischaemia was evaluated.

  DOI：

  10.1007/s00044-011-9726-x

文献信息

• Srivastava, Stuti; Goswami, Lalit N.; Dikshit, Dinesh K., Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2003, vol. 42, # 10, p. 2628 - 2631
  作者：Srivastava, Stuti、Goswami, Lalit N.、Dikshit, Dinesh K.

  DOI：——

  日期：——