(2R)-2-[(1S)-1,2-dihydroxyethyl]-3,4-bis(2-methoxyethoxymethoxy)-2H-furan-5-one | 1013404-65-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氢呋喃
• 英文名称: (2R)-2-[(1S)-1,2-dihydroxyethyl]-3,4-bis(2-methoxyethoxymethoxy)-2H-furan-5-one
• CAS: 1013404-65-3
• 化学式: C₁₄H₂₄O₁₀
• 分子量: 352.339
• InChiKey: UGDXQCVWEQEBGG-WDEREUQCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.6
• 重原子数：
  24
• 可旋转键数：
  14
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.79
• 拓扑面积：
  122
• 氢给体数：
  2
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  (2R)-2-[(1S)-1,2-dihydroxyethyl]-3,4-bis(2-methoxyethoxymethoxy)-2H-furan-5-one 在 4-二甲氨基吡啶 、 溶剂黄146 、 N,N-二异丙基乙胺 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 4.75h， 生成
  参考文献：
  名称：

  Design, synthesis and biological evaluation of brain targeting l-ascorbic acid prodrugs of ibuprofen with “lock-in” function

  摘要：

  A novel brain targeting L-ascorbic acid derivatives with "lock-in" function were designed and synthesized as prodrugs to achieve the effective delivery of ibuprofen to brain by glucose transporter 1 (GLUT(1)) and the Na+-dependent vitamin C transporter SVCT2. Ibuprofen-loaded four prodrugs were tested in the animals. Results from the in vivo distribution study after i.v. administration of these four prodrugs and naked ibuprofen indicated that four prodrugs exhibited excellent transport ability across the BBB and significantly increased the level of ibuprofen in brain. Among them, prodrugs 4 showed higher brain concentration. Both biodistribution data and pharmacokinetic parameters suggested that L-ascorbic acid thiamine disulfide delivery system was a promising carrier to enhance CNS drug's delivery ability into brain. (C) 2014 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2014.05.072
• 作为产物：
  描述：

  2-甲氧基乙氧基甲基氯 、 维生素 C 在 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 生成 (2R)-2-[(1S)-1,2-dihydroxyethyl]-3,4-bis(2-methoxyethoxymethoxy)-2H-furan-5-one
  参考文献：
  名称：

  抗坏血酸修饰的脑特异性脂质体给药系统具有“锁定”功能。

  摘要：

  在这项研究中，设计并合成了具有“锁定”功能的新型脑靶向抗坏血酸（AA）衍生物作为脂质体配体，以制备新型脂质体，以实现药物制剂通过葡萄糖转运蛋白1（GLUT 1）的有效递送。）和依赖Na +的维生素C转运蛋白（SVCT 2）。制备脂质体并根据粒径，ζ电势，包封效率，释放曲线，稳定性，溶血性和细胞毒性来表征。体内初步评估证明了与裸紫杉萜，未包被的和AA包被的脂质体相比，AA-硫胺素二硫化物系统（TDS）包被的脂质体具有改善的靶向能力，并显着增加了多西他赛（DTX）的脑部浓度。与裸紫杉萜相比，相对吸收效率和浓缩效率分别提高了3.24倍和5.62倍。分布数据和药代动力学参数均表明抗坏血酸硫胺素二硫化物输送系统是增强中枢神经系统（CNS）药物向大脑输送能力的有前途的载体。

  DOI：

  10.1016/j.chemphyslip.2019.01.005

文献信息

• Harnessing GLUT1‐Targeted Pro‐oxidant Ascorbate for Synergistic Phototherapeutics
  作者：Seyoung Koo、Min‐Goo Lee、Amit Sharma、Mingle Li、Xingcai Zhang、Kanyi Pu、Sung‐Gil Chi、Jong Seung Kim

  DOI：10.1002/anie.202110832

  日期：2022.4.19

  phototherapy. AA-EtNBS undergoes a reversible structural conversion of the ascorbate moiety in response to the redox environment, leading to a GLUT1-targeted pro-oxidant effect and synergistic phototherapeutic efficacy.

  5-O-取代的抗坏血酸-光敏剂偶联物AA-EtNBS证明了在 GLUT1 靶向抗癌光疗中利用抗坏血酸化学的好处。AA-EtNBS响应于氧化还原环境经历了抗坏血酸部分的可逆结构转换，导致 GLUT1 靶向促氧化作用和协同光疗功效。
• CN116966187
  申请人：——

  公开号：——

  公开（公告）日：——
• Ascorbic acid-modified brain-specific liposomes drug delivery system with “lock-in” function
  作者：Wenjiao Xiao、Qiuyi Fu、Yi Zhao、Li Zhang、Qiming Yue、Li Hai、Li Guo、Yong Wu

  DOI：10.1016/j.chemphyslip.2019.01.005

  日期：2019.11

  In this study, a novel brain targeting ascorbic acid (AA) derivative with “lock-in” function was designed and synthesized as a liposome ligand to prepare novel liposomes to achieve the effective delivery of drug formulations to brain via glucose transporter 1 (GLUT1) and the Na+-dependent vitamin C transporter (SVCT2). The liposome was prepared and characterized in terms of the particle size, zeta

  在这项研究中，设计并合成了具有“锁定”功能的新型脑靶向抗坏血酸（AA）衍生物作为脂质体配体，以制备新型脂质体，以实现药物制剂通过葡萄糖转运蛋白1（GLUT 1）的有效递送。）和依赖Na +的维生素C转运蛋白（SVCT 2）。制备脂质体并根据粒径，ζ电势，包封效率，释放曲线，稳定性，溶血性和细胞毒性来表征。体内初步评估证明了与裸紫杉萜，未包被的和AA包被的脂质体相比，AA-硫胺素二硫化物系统（TDS）包被的脂质体具有改善的靶向能力，并显着增加了多西他赛（DTX）的脑部浓度。与裸紫杉萜相比，相对吸收效率和浓缩效率分别提高了3.24倍和5.62倍。分布数据和药代动力学参数均表明抗坏血酸硫胺素二硫化物输送系统是增强中枢神经系统（CNS）药物向大脑输送能力的有前途的载体。
• Design, synthesis and biological evaluation of brain targeting l-ascorbic acid prodrugs of ibuprofen with “lock-in” function
  作者：Yi Zhao、Boyi Qu、Xueying Wu、Xiaocen Li、Qingqing Liu、Xiuxiu Jin、Li Guo、Li Hai、Yong Wu

  DOI：10.1016/j.ejmech.2014.05.072

  日期：2014.7

  A novel brain targeting L-ascorbic acid derivatives with "lock-in" function were designed and synthesized as prodrugs to achieve the effective delivery of ibuprofen to brain by glucose transporter 1 (GLUT(1)) and the Na+-dependent vitamin C transporter SVCT2. Ibuprofen-loaded four prodrugs were tested in the animals. Results from the in vivo distribution study after i.v. administration of these four prodrugs and naked ibuprofen indicated that four prodrugs exhibited excellent transport ability across the BBB and significantly increased the level of ibuprofen in brain. Among them, prodrugs 4 showed higher brain concentration. Both biodistribution data and pharmacokinetic parameters suggested that L-ascorbic acid thiamine disulfide delivery system was a promising carrier to enhance CNS drug's delivery ability into brain. (C) 2014 Elsevier Masson SAS. All rights reserved.