L-ascorbic acid-6 O-(S)-naproxen ester | 1192661-06-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: L-ascorbic acid-6 O-(S)-naproxen ester
• 英文别名: [(2S)-2-[(2R)-3,4-dihydroxy-5-oxo-2H-furan-2-yl]-2-hydroxyethyl] (2S)-2-(6-methoxynaphthalen-2-yl)propanoate
• CAS: 1192661-06-5
• 化学式: C₂₀H₂₀O₈
• 分子量: 388.374
• InChiKey: BDGLPHFNESROAS-XIWSCHCOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  28
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  123
• 氢给体数：
  3
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  在 palladium 10% on activated carbon 、 氢气 作用下， 以 甲醇 为溶剂， 反应 2.0h， 以80.8%的产率得到L-ascorbic acid-6 O-(S)-naproxen ester
  参考文献：
  名称：

  双脑靶向萘普生前药的设计、合成和神经保护作用

  摘要：

  设计并合成了一种新的双靶向萘普生前药，与葡萄糖和抗坏血酸共轭，用于中枢神经系统 (CNS) 药物递送，以有效地将萘普生递送至大脑。当与各种缓冲液、小鼠血浆和脑匀浆一起孵育时，萘普生可以从制备的前药中释放出来。此外，该前药在体内表现出优于萘普生的神经保护作用。我们的研究结果表明，用葡萄糖和抗坏血酸弹头对治疗剂进行化学修饰代表了一种利用弹头的内源性运输机制开发脑靶向前药的有前途和有效的策略。

  DOI：

  10.1002/ardp.201700382

文献信息

• Aryl (Ethanoic) Propanoic Acid Ascorbyl Ester, Preparation Method Thereof And Medicament Containing The Same
  申请人：Tang Luhong

  公开号：US20120115897A1

  公开（公告）日：2012-05-10

  The present invention designs and synthesizes the ascorbyl ester derivatives of the aryl (ethanoic) propanoic acid non-steroidal anti-inflammatory medicaments, such as ibuprofen, ketoprofen and naproxen, and addition salt of the derivatives with pharmaceutical acid or pharmaceutical alkaline. The non-steroidal anti-inflammatory medicament which takes the ibuprofen as the representative is a common antipyretic analgesic medicament. The invention has remarkable antipyretic and analgesic effects and good safety except for anti-inflammatory effect, thus being not only suitable for adults, but also suitable for the elderly people, infants and children. The aryl (ethanoic) propanoic acid ascorbyl ester can be converted into ascorbyl ester derivatives and the addition salts of the derivatives with pharmaceutical acid or pharmaceutical alkaline, which can improve the water solubility thereof, facilitate intravenously administration, reduce the onset time, improve the bioavailability, reduce the stimulation effect to gastrointestinal tract, and enhance the penetrating capacity to hemato encephalic barrier, and can be used as a novel medicament to be applied for antiphlogistic, antipyresis, analgesia, treatment of arthritis, dysmenorrheal, multiple sclerosis, pneumonia cystic fibrosis and patent ductus arteriosus of premature infants, and prevention and treatment of cerebral apoplexy, hypoxic-ischemic brain damage, senile dementia and certain cancers.

  本发明设计并合成了芳基（乙酸）丙酸非甾体抗炎药物，例如布洛芬、酮洛芬和萘普生的抗坏血酸酯衍生物，以及这些衍生物与药用酸或药用碱的加成盐。以布洛芬为代表的非甾体抗炎药是一种常见的解热镇痛药。本发明除了具有抗炎效果外，还具有显著的解热和镇痛效果，安全性良好，因此不仅适用于成人，也适用于老年人、婴幼儿。芳基（乙酸）丙酸抗坏血酸酯可转化为抗坏血酸酯衍生物以及这些衍生物与药用酸或药用碱的加成盐，这可以提高其水溶性，便于静脉给药，减少起效时间，提高生物利用度，减少对胃肠道的刺激作用，增强穿透血脑屏障的能力，并可作为新型药物应用于消炎、解热、镇痛、治疗关节炎、痛经、多发性硬化症、肺炎、囊性纤维化和早产儿动脉导管未闭，以及预防和治疗脑卒中、缺氧缺血性脑损伤、老年痴呆症和某些癌症。
• ASCORBIC ACID ARYL ACETATE/PROPIONATE ESTER, PREPARATION METHOD AND PHARMACEUTICAL COMPOSITION THEREOF
  申请人：Wuxi Hongrui Biomedical Technology Co., Ltd.

  公开号：EP2431361A1

  公开（公告）日：2012-03-21

  The present invention designs and synthesizes ascorbyl ester derivatives of aryl (ethanoic) propanoic acid non-steroidal anti-inflammatory medicaments, such as ibuprofen, ketoprofen and naproxen, and addition salt of the derivatives with pharmaceutical acid or pharmaceutical alkali. The non-steroidal anti-inflammatory medicament which takes the ibuprofen as the representative is a common antipyretic analgesic medicament. The invention has remarkable antipyretic and analgesic effects and good safety except for anti-inflammatory effect, thus being not only suitable for adults, but also suitable for elderly people, infants and children. The aryl (ethanoic) propanoic acid ascorbyl ester can be converted into ascorbyl ester derivatives and the addition salts of the derivatives with pharmaceutical acid or pharmaceutical alkali, which can improve the water solubility thereof, facilitate intravenously administration, reduce the onset time, improve the bioavailability, reduce the stimulation effect to gastrointestinal tract, and enhance the penetrating capacity to hemato encephalic barrier, and can be used as a novel medicament to be applied for antiphlogistic, antipyresis, analgesia, treatment of arthritis, dysmenorrheal, multiple sclerosis, pneumonia cystic fibrosis and patent ductus arteriosus of premature infants, and prevention and treatment of cerebral apoplexy, hypoxic-ischemic brain damage, senile dementia and certain cancers.

  本发明设计合成了布洛芬、酮洛芬、萘普生等芳基（乙）丙酸类非甾体抗炎药物的抗坏血酸酯衍生物，以及衍生物与药用酸或药用碱的加成盐。以布洛芬为代表的非甾体抗炎药物是一种常用的解热镇痛药物。本发明除消炎作用外，解热镇痛效果显著，安全性好，不仅适用于成人，也适用于老人、婴幼儿。芳基（乙）丙酸抗坏血酸酯可转化为抗坏血酸酯衍生物及衍生物与药用酸或药用碱的加成盐，可提高其水溶性，便于静脉给药，缩短起效时间，提高生物利用度，减少对胃肠道的刺激作用、可作为新型药物应用于抗抑郁、镇痛、治疗关节炎、痛经、多发性硬化、肺炎囊性纤维化和早产儿动脉导管未闭，以及预防和治疗脑中风、缺氧缺血性脑损伤、老年性痴呆和某些癌症。
• US8703975B2
  申请人：——

  公开号：US8703975B2

  公开（公告）日：2014-04-22