N-(2-aminoethyl)-2-[(2R,3R,4R,5R)-2-(2,4-dioxopyrimidin-1-yl)-4-hydroxy-5-(hydroxymethyl)oxolan-3-yl]oxyacetamide | 1207847-55-9

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘧啶核苷
• 英文名称: N-(2-aminoethyl)-2-[(2R,3R,4R,5R)-2-(2,4-dioxopyrimidin-1-yl)-4-hydroxy-5-(hydroxymethyl)oxolan-3-yl]oxyacetamide
• CAS: 1207847-55-9
• 化学式: C₁₃H₂₀N₄O₇
• 分子量: 344.324
• InChiKey: MFDILBHAMQRNKF-FAQVLOEFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -3
• 重原子数：
  24
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  163
• 氢给体数：
  5
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  2'-O-methoxycarbonylmethyluridine 、 乙二胺 以 乙醇 为溶剂， 反应 12.0h， 以60%的产率得到N-(2-aminoethyl)-2-[(2R,3R,4R,5R)-2-(2,4-dioxopyrimidin-1-yl)-4-hydroxy-5-(hydroxymethyl)oxolan-3-yl]oxyacetamide
  参考文献：
  名称：

  Synthesis and Properties of Oligodeoxyribonucleotides Bearing a Polyamino Group at the 2′ Position via 2′-O-Carbamoylmethyl and 2′-S-Carbamoylmethyl groups

  摘要：

  An oligodeoxyribonucleotide containing 2'-O-methoxycarbonylmethyluridine was synthesized and converted into several 2'-modified oligodeoxyribonucleotides by a postsynthetic modification method. Using this method, oligodeoxyribonucleotides bearing a polyamine at the 2' Position were easily prepared, which could form duplexes with either complementary DNA or RNA.

  DOI：

  10.1080/15257770903307185

文献信息

• Cell-Penetrating Oligonucleotides
  申请人：OLIGOMER SCIENCES AB

  公开号：US20160008389A1

  公开（公告）日：2016-01-14

  The present invention relates to modified oligonucleotides of 5-50 nucleotide residues, wherein at least 25% of the nucleotides are independently modified at the 2′ position to comprise the structure of formula (I), wherein base is a purine or pyrimidine moiety; and R 1 , R 2 , R 3 , R 4 , p and q are as defined in the description. The modified oligonucleotides comprising said structures are useful as medicaments for enhancement of drug uptake in oligonucleotide based therapy in humans and animals.

  本发明涉及5-50个核苷酸残基的修饰寡核苷酸，其中至少25％的核苷酸在2'位独立修饰，包括式（I）的结构，其中碱基是嘌呤或嘧啶基团；且R1，R2，R3，R4，p和q如描述中所定义。包含所述结构的修饰寡核苷酸在人类和动物的寡核苷酸基治疗中用作增强药物摄取的药物。
• CELL-PENETRATING OLIGONUCLEOTIDES
  申请人：Oligomer Sciences AB

  公开号：EP2961757A1

  公开（公告）日：2016-01-06
• US9463200B2
  申请人：——

  公开号：US9463200B2

  公开（公告）日：2016-10-11
• [EN] CELL-PENETRATING OLIGONUCLEOTIDES<br/>[FR] OLIGONUCLÉOTIDES PÉNÉTRANT LES CELLULES
  申请人：OLIGOMER SCIENCES AB

  公开号：WO2014131892A1

  公开（公告）日：2014-09-04

  The present invention relates to modified oligonucleotides of 5-50 nucleotide residues, wherein at least 25% of the nucleotides are independently modified at the 2' position to comprise the structure of formula (I), wherein base is a purine or pyrimidine moiety; and R1, R2, R3, R4, p and q are as defined in the description. The modified oligonucleotides comprising said structures are useful as medicaments for enhancement of drug uptake in oligonucleotide based therapy in humans and animals.
• Synthesis and Properties of Oligodeoxyribonucleotides Bearing a Polyamino Group at the 2′ Position via 2′-<i>O</i>-Carbamoylmethyl and 2′-<i>S</i>-Carbamoylmethyl groups
  作者：Hiroaki Ozaki、Shingo Nomura、Shingo Momiyama、Kazuyuki Yokotsuka、Masayasu Kuwahara、Hiroaki Sawai

  DOI：10.1080/15257770903307185

  日期：2009.10.28

  An oligodeoxyribonucleotide containing 2'-O-methoxycarbonylmethyluridine was synthesized and converted into several 2'-modified oligodeoxyribonucleotides by a postsynthetic modification method. Using this method, oligodeoxyribonucleotides bearing a polyamine at the 2' Position were easily prepared, which could form duplexes with either complementary DNA or RNA.