N-[3-[4-[3-azidopropyl-(2,2,2-trifluoroacetyl)amino]butyl-(2,2,2-trifluoroacetyl)amino]propyl]-2,2,2-trifluoroacetamide | 1190203-79-2

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: N-[3-[4-[3-azidopropyl-(2,2,2-trifluoroacetyl)amino]butyl-(2,2,2-trifluoroacetyl)amino]propyl]-2,2,2-trifluoroacetamide
• CAS: 1190203-79-2
• 化学式: C₁₆H₂₁F₉N₆O₃
• 分子量: 516.367
• InChiKey: KVWOIXXMITZZTR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  34
• 可旋转键数：
  13
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.81
• 拓扑面积：
  84.1
• 氢给体数：
  1
• 氢受体数：
  14

反应信息

• 作为反应物：
  描述：

  N-[3-[4-[3-azidopropyl-(2,2,2-trifluoroacetyl)amino]butyl-(2,2,2-trifluoroacetyl)amino]propyl]-2,2,2-trifluoroacetamide 、 5-ethynyl-5’-dimethoxytrityl-2’-O-methyluridine 在 copper(ll) sulfate pentahydrate 、 sodium ascorbate 作用下， 以 水 、 叔丁醇 为溶剂， 以65%的产率得到
  参考文献：
  名称：

  通过更快的靶结合动力学来寻求改进的寡核苷酸治疗方法

  摘要：

  大自然启发的RNA修饰，可实现更快的杂交：使用三唑接头将精胺基团与2'- O-甲基寡核糖核苷酸核苷酸结合，可加速与互补RNA的结合。主沟中的缀合片段模仿天然多胺与细胞RNA的作用，并大大提高了杂交亲和力。

  DOI：

  10.1002/chem.201701670
• 作为产物：
  描述：

  精胺 在 吡啶 、 copper(ll) sulfate pentahydrate 、 triflic azide 、 三乙胺 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 38.0h， 生成 N-[3-[4-[3-azidopropyl-(2,2,2-trifluoroacetyl)amino]butyl-(2,2,2-trifluoroacetyl)amino]propyl]-2,2,2-trifluoroacetamide
  参考文献：
  名称：

  Versatile Site-Specific Conjugation of Small Molecules to siRNA Using Click Chemistry

  摘要：

  We have previously demonstrated that conjugation of small molecule ligands to small interfering RNAs (siRNAs) and anti-microRNAs results in functional siRNAs and antagomirs in vivo. Here we report on the development of an efficient chemical strategy to make oligoribonucleotide-ligand conjugates using the copper-catalyzed azide-alkyne cycloaddition (CuAAC) or click reaction. Three click reaction approaches were evaluated for their feasibility and suitability for high-throughput synthesis: the CuAAC reaction at the monomer level prior to oligonucleotide synthesis, the solution-phase postsynthetic "click conjugation", and the "click conjugation" on an immobilized and cornpletely protected alkyne-oligonucleotide scaffold. Nucleosides bearing 5'-alkyne moieties were used for conjugation to the 5'-end of the oligonucleotide. Previously described 2'- and 3'-O-propargylated nucleosides were prepared to introduce the alkyne moiety to the 3' and 5' termini and to the internal positions of the scaffold. Azido-functionalized ligands bearing lipophilic long chain alkyls, cholesterol, oligoamine, and carbohydrate were utilized to study the effect of physicochemical characteristics of the incoming azide on click conjugation to the alkyne-oligonucleotide scaffold in solution and on immobilized solid support. We found that microwave-assisted click conjugation of azido-functionalized ligands to a fully protected solid-support bound alkyne-oligonucleotide prior to deprotection was the most efficient "click conjugation" strategy for site-specific, high-throughput oligonucleotide conjugate synthesis tested. The siRNA conjugates synthesized using this approach effectively silenced expression of a luciferase gene in a stably transformed HeLa cell line.

  DOI：

  10.1021/jo101761g

文献信息

• Site specific delivery of nucleic acids by combining targeting ligands with endosomolytic components
  申请人：Tekmira Pharmaceuticals Corporation

  公开号：US09345780B2

  公开（公告）日：2016-05-24

  The invention relates to compositions and methods for site-specific delivery of nucleic acids by combining them with targeting ligands and endosomolytic components.

  这项发明涉及将核酸与靶向配体和内体溶解组分结合，用于特定位点递送核酸的组合物和方法。
• CHEMICAL MODIFICATIONS OF MONOMERS AND OLIGONUCLEOTIDES WITH CYCLOADDITION
  申请人：ALNYLAM PHARMACEUTICALS, INC.

  公开号：US20150203847A1

  公开（公告）日：2015-07-23

  The invention features compounds of formula I or II: In one embodiment, the invention relates compounds and processes for conjugating ligand to oligonucleotide. The invention further relates to methods for treating various disorders and diseases such as viral infections, bacterial infections, parasitic infections, cancers, allergies, autoimmune diseases, immunodeficiencies and immunosuppression.

  这项发明涉及公式I或II的化合物。在一个实施例中，本发明涉及化合物和将配体与寡核苷酸结合的过程。本发明还涉及用于治疗各种疾病和疾病的方法，例如病毒感染，细菌感染，寄生虫感染，癌症，过敏，自身免疫疾病，免疫缺陷和免疫抑制。
• SITE-SPECIFIC DELIVERY OF NUCLEIC ACIDS BY COMBINING TARGETING LIGANDS WITH ENDOSOMOLYTIC COMPONENTS
  申请人：Manoharan Muthiah

  公开号：US20110123520A1

  公开（公告）日：2011-05-26

  The invention relates to compositions and methods for site-specific delivery of nucleic acids by combining them with targeting ligands and endosomolytic components.
• US20140256785A1
  申请人：——

  公开号：US20140256785A1

  公开（公告）日：2014-09-11
• US8575123B2
  申请人：——

  公开号：US8575123B2

  公开（公告）日：2013-11-05