3,4,5-tris(2-(2-(2-azidoethoxy)ethoxy)ethoxy)benzoic acid | 350483-40-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 3,4,5-tris(2-(2-(2-azidoethoxy)ethoxy)ethoxy)benzoic acid
• 英文别名: 3,4,5-tris[2-[2-(2-azidoethoxy)ethoxy]ethoxy]benzoic acid
• CAS: 350483-40-8
• 化学式: C₂₅H₃₉N₉O₁₁
• 分子量: 641.638
• InChiKey: RDAUNQMPQYPUAB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  45
• 可旋转键数：
  31
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.72
• 拓扑面积：
  163
• 氢给体数：
  1
• 氢受体数：
  17

反应信息

• 作为反应物：
  描述：

  3,4,5-tris(2-(2-(2-azidoethoxy)ethoxy)ethoxy)benzoic acid 在 palladium 10% on activated carbon 、 氢气 作用下， 以 乙醇 为溶剂， 以79%的产率得到3,4,5-Tris[2-[2-(2-aminoethoxy)ethoxy]ethoxy]benzoic acid
  参考文献：
  名称：

  Okuro, Kou; Kinbara, Kazushi; Tsumoto, Kouhei, Journal of the American Chemical Society, 2009, vol. 131, p. 1626 - 1627

  摘要：

  DOI：
• 作为产物：
  描述：

  8-azido-3,6-dioxaoctyl tosylate 在 水 、 potassium carbonate 、 sodium hydroxide 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 44.5h， 生成 3,4,5-tris(2-(2-(2-azidoethoxy)ethoxy)ethoxy)benzoic acid
  参考文献：
  名称：

  Efficient Tandem Copper‐Catalyzed Click Synthesis of Multisugar‐Modified Oligonucleotides

  摘要：

  Nucleic acids in the form of siRNA, antisense oligonucleotides or mRNA are currently explored as new promising modalities in the pharmaceutical industry. Particularly, the success of mRNA‐vaccines against SARS‐CoV‐2, along with the successful development of the first sugar‐modified siRNA therapeutics has inspired the field. The development of nucleic acid therapeutics requires efficient chemistry to link oligonucleotides to chemical structures that can improve stability, boost cellular uptake, or enable specific targeting. For the siRNA therapeutics currently in use, modification of the 3′‐end of the oligonucleotides with triple‐N‐acetylgalactosamine (GalNAc)3 was shown to be of significance. This modification is currently achieved through cumbersome multistep synthesis and subsequent loading onto the solid support material. Herein, we report the development of a bifunctional click‐reactive linker that allows the modification of oligonucleotides in a tandem click reaction with multiple sugars, regardless of the position within the oligonucleotide, with remarkable efficiency and in a one‐pot reaction.

  DOI：

  10.1002/anie.202405161

文献信息

• MULTI-FLUORESCENT SUBSTANCE INCLUDING NOVEL COUMARIN DERIVATIVE, AND LED LIGHT SOURCE-BASED MICROFLUORESCENT QUANTITATIVE BIOSENSOR FOR DIAGNOSIS USING SAME
  申请人：Park Hyun

  公开号：US20140350227A1

  公开（公告）日：2014-11-27

  The present invention relates to a novel coumarin derivative, to a method for preparing the same, and a multi-fluorescent substance that includes a plurality of the coumarin derivatives and is able to emit light using an LED light source. A novel coumarin derivative multi-fluorescent substance according to the present invention has an optimal emission wavelength band of 512 nm to 590 nm and thereby is effective in improving a signal intensity and stability since light emission using an LED light source is possible. In addition, higher fluorescence reactivity is exhibited compared to coumarin fluorescent substances known in the related arts since one molecule has a plurality of fluorescent substances, and the problem of the coumarin fluorescent substance possibly binding to a binding site of the antigen of the antibody is solved since fluorescence detection is possible even when a minimum number of fluorescent substance molecules bind to an antibody. Moreover, the novel coumarin derivative multi-fluorescent substance according to the present invention is suitably used in a fluorescent-linked immunosorbent assay (FLISA) and a rapid fluorescent immunochromatographic test (FICT) as an LED-based microfluorescent quantitative biosensor for diagnosis, therefore, diseases such as malaria may be rapidly and quantitatively analyzed.

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  日期：2021.4

  (PDT) is a promising approach for the targeted treatment of cancer and various other human disorders. An effective, clinically approved approach in PDT involves the administration of 5-aminolevulinic acid (ALA) to generate elevated levels of the natural photosensitiser protoporphyrin IX (PpIX). The development of prodrugs of ALA is of considerable interest as a means to enhance the efficiency and cell

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  DOI：10.1021/jacs.7b13614

  日期：2018.2.21

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• Tuning the Size of Nanoassembles: A Hierarchical Transfer of Information from Dendrimers to Polyion Complexes
  作者：Sandra P. Amaral、Maun H. Tawara、Marcos Fernandez‐Villamarin、Erea Borrajo、José Martínez‐Costas、Anxo Vidal、Ricardo Riguera、Eduardo Fernandez‐Megia

  DOI：10.1002/anie.201712244

  日期：2018.5.4

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• Design and Synthesis of a Multivalent Heterobifunctional CD22 Ligand as a Potential Immunomodulator
  作者：Hajjaj Abdu-Allah、Makoto Kiso、Kozo Watanabe、Shusaku Daikoku、Osamu Kanie、Takeshi Tsubata、Hiromune Ando、Hideharu Ishida

  DOI：10.1055/s-0030-1260151

  日期：2011.9

  We describe the design and synthesis of a trivalent CD22 ligand conjugated with a trivalent nitrophenol (ligand for decameric anti-nitrophenol immunoglobulin M). To generate such a bifunctional ligand, we designed and prepared two synthetic building blocks possessing different terminal functionalities. Coupling of these compounds afforded a trivalent azide-terminated scaffold. Ligation of the scaffold with an alkyne-terminated CD22 ligand by the use of click chemistry afforded the target trivalent cluster. We anticipate that our ligand will be valuable in a variety of applications, including targeting B cells and modulation of the humoral immune response.

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