(S)-1-(2-(1-(4-chlorobenzoyl)-5-methoxy-2-methyl-1H-indol-3-yl)acetyl)pyrrolidine-2-carboxylic acid | 908243-79-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: (S)-1-(2-(1-(4-chlorobenzoyl)-5-methoxy-2-methyl-1H-indol-3-yl)acetyl)pyrrolidine-2-carboxylic acid
• CAS: 908243-79-8
• 化学式: C₂₄H₂₃ClN₂O₅
• 分子量: 454.91
• InChiKey: OGPRUTKTXHIAPJ-NRFANRHFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.92
• 重原子数：
  32.0
• 可旋转键数：
  5.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  88.84
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  (S)-1-(2-(1-(4-chlorobenzoyl)-5-methoxy-2-methyl-1H-indol-3-yl)acetyl)pyrrolidine-2-carboxylic acid 、 L-半胱氨酸乙酯盐酸盐 在 N,N'-羰基二咪唑 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 以30%的产率得到ethyl (2R)-2-((2S)-1-(2-(1-(4-chlorobenzoyl)-5-methoxy-2-methyl-1H-indol-3-yl)acetyl)pyrrolidine-2-carboxamido)-3-mercaptopropanoate
  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
• 作为产物：
  描述：

  吲哚美辛 在 草酰氯 、 sodium hydroxide 作用下， 以 二氯甲烷 、 水 为溶剂， 生成 (S)-1-(2-(1-(4-chlorobenzoyl)-5-methoxy-2-methyl-1H-indol-3-yl)acetyl)pyrrolidine-2-carboxylic acid
  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

• Synthesis and pharmacochemical study of novel polyfunctional molecules combining anti-inflammatory, antioxidant, and hypocholesterolemic properties
  作者：Christos M. Doulgkeris、Dimitrios Galanakis、Angeliki P. Kourounakis、Karyofyllis C. Tsiakitzis、Antonios M. Gavalas、Phaedra T. Eleftheriou、Panagiotis Victoratos、Eleni A. Rekka、Panos N. Kourounakis

  DOI：10.1016/j.bmcl.2005.11.027

  日期：2006.2

  We have designed and synthesized a series of novel molecules having a residue of a classical NSAID and an antioxidant moiety, both attached through amide bonds to a known nootropic structure, an L-proline, frans-4-hydroxy-L-proline or DL-pipecolinic acid residue. The compounds were found to retain anti-inflammatory and antioxidant activities, to acquire hypocholesterolemic action, and to possess a greatly reduced gastrointestinal toxicity. The novel molecules could find useful applications, among others, in slowing the progression or delaying the onset of neurodegenerative diseases. (c) 2005 Elsevier Ltd. All rights reserved.
• WO2006/90192
  申请人：——

  公开号：——

  公开（公告）日：——