3,4,5-tris(benzyloxy)-N-(2-(5-methoxy-1H-indol-3-yl)ethyl)benzamide | 1366075-52-6

• 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: 3,4,5-tris(benzyloxy)-N-(2-(5-methoxy-1H-indol-3-yl)ethyl)benzamide
• 英文别名: 3,4,5-tris(benzyloxy)-N-(2-(5-methox-1H-indol-3-yl)ethyl)benzamide；3, 4, 5-tris(benzyloxy)-N-(2-(5-methoxy-1H-indol-3-yl)ethyl)benzamide；N-[2-(5-methoxy-1H-indol-3-yl)ethyl]-3,4,5-tris(phenylmethoxy)benzamide
• CAS: 1366075-52-6
• 化学式: C₃₉H₃₆N₂O₅
• 分子量: 612.725
• InChiKey: NYNKGEUUYRMQNS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.6
• 重原子数：
  46
• 可旋转键数：
  14
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  81.8
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3,4,5-tris(benzyloxy)-N-(2-(5-methoxy-1H-indol-3-yl)ethyl)benzamide 在 palladium 10% on activated carbon 、 氢气 作用下， 以 甲醇 、 氯仿 为溶剂， 反应 2.0h， 生成 3,4,5-trihydroxy-N-(2-(5-methoxy-1H-indol-3-yl)ethyl)benzamide
  参考文献：
  名称：

  Tryptamine-Gallic Acid Hybrid Prevents Non-steroidal Anti-inflammatory Drug-induced Gastropathy

  摘要：

  We have investigated the gastroprotective effect of SEGA (3a), a newly synthesized tryptamine-gallic acid hybrid molecule against non-steroidal anti-inflammatory drug (NSAID)-induced gastropathy with mechanistic details. SEGA (3a) prevents indomethacin (NSAID)-induced mitochondrial oxidative stress (MOS) and dysfunctions in gastric mucosal cells, which play a pathogenic role in inducing gastropathy. SEGA (3a) offers this mitoprotective effect by scavenging of mitochondrial superoxide anion (O(2)(·-)) and intramitochondrial free iron released as a result of MOS. SEGA (3a) in vivo blocks indomethacin-mediated MOS, as is evident from the inhibition of indomethacin-induced mitochondrial protein carbonyl formation, lipid peroxidation, and thiol depletion. SEGA (3a) corrects indomethacin-mediated mitochondrial dysfunction in vivo by restoring defective electron transport chain function, collapse of transmembrane potential, and loss of dehydrogenase activity. SEGA (3a) not only corrects mitochondrial dysfunction but also inhibits the activation of the mitochondrial pathway of apoptosis by indomethacin. SEGA (3a) inhibits indomethacin-induced down-regulation of bcl-2 and up-regulation of bax genes in gastric mucosa. SEGA (3a) also inhibits indometacin-induced activation of caspase-9 and caspase-3 in gastric mucosa. Besides the gastroprotective effect against NSAID, SEGA (3a) also expedites the healing of already damaged gastric mucosa. Radiolabeled ((99m)Tc-labeled SEGA (3a)) tracer studies confirm that SEGA (3a) enters into mitochondria of gastric mucosal cell in vivo, and it is quite stable in serum. Thus, SEGA (3a) bears an immense potential to be a novel gastroprotective agent against NSAID-induced gastropathy.

  DOI：

  10.1074/jbc.m111.307199
• 作为产物：
  描述：

  氯化苄 在 乙醇 、 叔丁胺氢碘酸盐 、 potassium carbonate 、 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 、 potassium hydroxide 作用下， 以 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 反应 8.0h， 生成 3,4,5-tris(benzyloxy)-N-(2-(5-methoxy-1H-indol-3-yl)ethyl)benzamide
  参考文献：
  名称：

  TRYPTAMINE DERIVATIVES, THEIR PREPARATION AND THEIR USE IN GASTROPATHY

  摘要：

  不同色胺衍生物的合成和胃保护效果的评估。色胺衍生物通过与一些已知抗氧化分子形成酰胺或酯而被合成。这些衍生物在体外表现出优秀的抗氧化性能。在所有衍生物中，通过将血清素与没食子酸结合而制备的SEGA（3a）化合物在体内和体外都表现出比其他合成化合物更强的抗氧化性能。SEGA（3a）呈剂量依赖性地显示对NSAIDs（消炎药，如消炎痛或双氯芬酸）诱导的胃病的胃保护作用，并且加速了受伤部位的愈合。它预防了NSAIDs诱导的体内线粒体氧化应激。该衍生物通过阻止caspase 9和caspase-3的激活，恢复NSAIDs介导的线粒体跨膜电位崩溃和脱氢酶活性，从而预防了NSAIDs诱导的线粒体氧化应激介导的凋亡。SEGA（3a）不仅作为铁螯合剂，还作为线粒体内ROS清除剂起作用。因此，SEGA（3a）是一种有效预防NSAID诱导的胃病以及压力或酒精介导的胃损伤的抗氧化抗凋亡分子。

  公开号：

  US20130197052A1

文献信息

• Tryptamine derivatives, their preparation and their use in gastropathy
  申请人：Bandyopadhyay Uday

  公开号：US08901317B2

  公开（公告）日：2014-12-02

  The synthesis and evaluation of gastroprotective effect of different tryptamine derivatives. Tryptamine derivatives have been synthesized by formation of amide or ester with some known anti oxidant molecules. These derivatives show excellent antioxidant property in vitro. Among all the derivatives the compound SEGA (3a), that was prepared by the combination of serotonin with gallic acid shows the greater antioxidant property than the other synthesized compounds both in vivo and in vitro. SEGA(3a) shows the gastroprotective effect against NSAIDs (indomethacin or diclofenac)-induced gastropathy in dose dependent manner and also accelerates the healing from injury. It prevents the NSAIDs-induced mitochondrial oxidative stress in vivo. This derivative prevents NSAID-induced mitochondrial oxidative stress-mediated apoptosis in vivo by preventing the activation of caspase 9 and caspase-3 and restores NSAIDs-mediated collapse of mitochondroial transmembrane potential and dehydrogenase activity. SEGA (3a) plays an important role as an iron chelator as well as intra mitochondrial ROS scavenger. Thus, SEGA (3a) is a potent antioxidant antiapototic molecule, which efficiently prevents NSAID-induced gastropathy and stress or alcohol-mediated gastric damage.

  不同色胺衍生物的合成和胃保护效应的评价。通过与一些已知的抗氧化分子形成酰胺或酯的方式合成了色胺衍生物。这些衍生物在体外表现出优异的抗氧化性能。在所有衍生物中，通过将血清素与没食子酸结合制备的化合物SEGA（3a）在体内外表现出比其他合成的化合物更强的抗氧化性能。SEGA（3a）表现出剂量依赖性的对NSAIDs（消炎药indomethacin或diclofenac）诱导的胃病的胃保护作用，并加速伤口愈合。它可以预防NSAIDs诱发的线粒体氧化应激。这种衍生物通过防止caspaSE 9和caspaSE-3的激活，并恢复NSAIDs介导的线粒体跨膜电位和脱氢酶活性的崩塌，从而预防NSAIDs诱导的线粒体氧化应激介导的凋亡。SEGA（3a）在铁螯合剂以及线粒体内ROS清除剂方面发挥重要作用。因此，SEGA（3a）是一种有效预防NSAIDs诱导的胃病和应激或酒精诱导的胃损伤的强效抗氧化和抗凋亡分子。
• US8901317B2
  申请人：——

  公开号：US8901317B2

  公开（公告）日：2014-12-02