2-(((benzyloxy)carbonyl)amino)-2-((((S)-2-(6-methoxynaphthalen-2-yl)propanoyl)oxy)methyl)propane-1,3-diyl (2S,2'S)-bis(2-(6-methoxynaphthalen-2-yl)propanoate) | 1228151-32-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2-(((benzyloxy)carbonyl)amino)-2-((((S)-2-(6-methoxynaphthalen-2-yl)propanoyl)oxy)methyl)propane-1,3-diyl (2S,2'S)-bis(2-(6-methoxynaphthalen-2-yl)propanoate)
• CAS: 1228151-32-3
• 化学式: C₅₄H₅₃NO₁₁
• 分子量: 892.015
• InChiKey: MQEFSGAICCLZER-KVBYWJEESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.18
• 重原子数：
  66.0
• 可旋转键数：
  18.0
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  144.92
• 氢给体数：
  1.0
• 氢受体数：
  11.0

反应信息

• 作为反应物：
  描述：

  2-(((benzyloxy)carbonyl)amino)-2-((((S)-2-(6-methoxynaphthalen-2-yl)propanoyl)oxy)methyl)propane-1,3-diyl (2S,2'S)-bis(2-(6-methoxynaphthalen-2-yl)propanoate) 在 palladium on activated charcoal 、 氢气 作用下， 生成 2-amino-2-((((S)-2-(6-methoxynaphthalen-2-yl)propanoyl)oxy)methyl)propane-1,3-diyl (2S,2'S)-bis(2-(6-methoxynaphthalen-2-yl)propanoate)
  参考文献：
  名称：

  Design, synthesis and biological evaluation of enzymatically cleavable NSAIDs prodrugs derived from self-immolative dendritic scaffolds for the treatment of inflammatory diseases

  摘要：

  It has been reported that delivery systems based on dendritic prodrugs of Nonsteroidal Anti-Inflammatory Drugs (NSAIDs) improved the properties of drug molecules and reduced the side effects and irritation on the gastric mucosa. To find a more effective way in NSAIDs dendritic prodrugs, in this paper, three different dendritic scaffolds of enzymatically cleavable naproxen conjugates have been synthesized in a convergent approach and well characterized by NMR and MS techniques. These self-immolative dendritic NISADs prodrugs programmed to release multiple molecules of the potent naproxen after a single enzymatic activation step, and in 50% human plasma, the drug released from the compound T3 reaching 47.3% after 24 h in vitro assay. Moreover, all prodrugs were also found to maintain more significant anti-inflammatory activity, no significant cytotoxicity against HEK293 cells and less degree of ulcerogenic potential in vivo than their monomeric counterpart naproxen. These results provided an effective entry to the development of new dendritic NSAIDs prodrugs. Crown Copyright (C) 2013 Published by Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2013.05.006
• 作为产物：
  描述：

  萘普生 、 [2-羟基-1,1-二(羟甲基)乙基]氨基甲酸苄酯 在 4-二甲氨基吡啶 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 以94.4%的产率得到2-(((benzyloxy)carbonyl)amino)-2-((((S)-2-(6-methoxynaphthalen-2-yl)propanoyl)oxy)methyl)propane-1,3-diyl (2S,2'S)-bis(2-(6-methoxynaphthalen-2-yl)propanoate)
  参考文献：
  名称：

  Design, synthesis and biological evaluation of enzymatically cleavable NSAIDs prodrugs derived from self-immolative dendritic scaffolds for the treatment of inflammatory diseases

  摘要：

  It has been reported that delivery systems based on dendritic prodrugs of Nonsteroidal Anti-Inflammatory Drugs (NSAIDs) improved the properties of drug molecules and reduced the side effects and irritation on the gastric mucosa. To find a more effective way in NSAIDs dendritic prodrugs, in this paper, three different dendritic scaffolds of enzymatically cleavable naproxen conjugates have been synthesized in a convergent approach and well characterized by NMR and MS techniques. These self-immolative dendritic NISADs prodrugs programmed to release multiple molecules of the potent naproxen after a single enzymatic activation step, and in 50% human plasma, the drug released from the compound T3 reaching 47.3% after 24 h in vitro assay. Moreover, all prodrugs were also found to maintain more significant anti-inflammatory activity, no significant cytotoxicity against HEK293 cells and less degree of ulcerogenic potential in vivo than their monomeric counterpart naproxen. These results provided an effective entry to the development of new dendritic NSAIDs prodrugs. Crown Copyright (C) 2013 Published by Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2013.05.006

文献信息

• Synthesis of first generation Janus-Type dendrimers bearing Asp oligopeptides and naproxen
  作者：Liang Ouyang、Lifang Ma、Yanhua Li、Junzhu Pan、Li Guo

  DOI：10.3998/ark.5550190.0011.221

  日期：——

  To construct a water-soluble and bone-targeting non-steroidal anti-inflammatory dendritic drug carrier, a series of Asp oligopeptides and naproxen based poly amido-ester Janus dendrimers were synthesized using a conventional method and their water solubility was preliminary evaluated. The corresponding small dendritic linkers contain two or three drug moieties on the surface and two or three oligopeptides groups at the focal terminus. This design provided an effective entry for the synthesis of multiple drug carriers with water-soluble and bone-targeting.