中氮茚,八氢-8-甲氧基-1,6,7-三(苯基甲氧基)-,1S-(1.α.,6.β.,7.α.,8.β.,8a.β.)- | 127517-38-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 中氮茚,八氢-8-甲氧基-1,6,7-三(苯基甲氧基)-,1S-(1.α.,6.β.,7.α.,8.β.,8a.β.)-
• 中文别名: 5-[(2R,4S,5S)-4-叠氮基-5-(羟基甲基)四氢呋喃-2-基]-1-甲基嘧啶-2,4-二酮
• 英文名称: 3'-azido-2',3'-dideoxy-1-methylpseudouridine
• 英文别名: 1-Methyl-5-(3-azido-2,3-dideoxy-beta-pentofuranosyl)uracil；5-[(2R,4S,5S)-4-azido-5-(hydroxymethyl)oxolan-2-yl]-1-methylpyrimidine-2,4-dione
• CAS: 127517-38-8
• 化学式: C₁₀H₁₃N₅O₄
• 分子量: 267.244
• InChiKey: UTJZDXBVQJNTHL-XLPZGREQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.6
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  93.2
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  3'-azido-2',3'-dideoxy-5'-O-trityl-1-methylpseudouridine 在 溶剂黄146 作用下， 以91%的产率得到中氮茚,八氢-8-甲氧基-1,6,7-三(苯基甲氧基)-,1S-(1.α.,6.β.,7.α.,8.β.,8a.β.)-
  参考文献：
  名称：

  Nucleosides. 153. Synthesis of 1-methyl-5-(3-azido-2,3-dideoxy-.beta.-D-erythro-pentofuranosyl)uracil and 1-methyl-5-(3-azido-2,3-dideoxy-2-fluoro-.beta.-D-arabinofuranosyl)uracil. The C-nucleoside isostere of 3'-azido-3'-deoxythymidine and its 2'-"up"-fluoro analog

  摘要：

  1-Methyl-5-(3-azido-2,3-dideoxy-beta-D-erythro-pentofuranosyl)uracil (C-AZT), a C-nucleoside isostere of the potent anti-AIDS nucleoside 3'-azido-3'-deoxythymidine (AZT), was synthesized. 1-Methyl-2'-deoxy-5'-O-tritylpseudouridine (2a) was oxidized with CrO3/pyridine/Ac2O complex to 1-methyl-5-(5-O-trityl-beta-D-glycero-pentofuranos-3-ulosyl) uracil (12a), which was selectively reduced to 1-methyl-5-(5-O-trityl-beta-D-threo-pentofuranosyl)uracil (13a). Mesylation of 13a to 14a followed by nucleophilic displacement of the mesyloxy group with azide afforded 3'-azido-2',3'-dideoxy-5'-O-trityl-1-methylpseudoridine (15a), which was detritylated to C-AZT. In a similar manner, 1-methyl-5-(2-deoxy-2-fluoro-beta-D-arabinofuranosyl)uracil (C-FMAU, a potent antiherpetic nucleoside) was converted into the 3'-azido analogue (3'-azido-C-FMAU). Both C-AZT and 3'-azido-C-FMAU, however, did not exhibit any significant inhibitory activity against HIV in H9 cells.

  DOI：

  10.1021/jm00169a030

文献信息

• [EN] NUCLEIC ACID CHEMICAL MODIFICATIONS<br/>[FR] MODIFICATIONS CHIMIQUES D'ACIDE NUCLÉIQUE
  申请人：ALNYLAM PHARMACEUTICALS INC

  公开号：WO2010101951A1

  公开（公告）日：2010-09-10

  he present invention provides nucleosides of formula (1) and oligonucleotides comprising at least on nucleoside of formula (2): Another aspect of the invention relates to a method of inhibiting the expression of a gene in cell, the method comprising (a) contacting an oligonucleotide of the invention with the cell; and (b) maintaining the cell from step (a) for a time sufficient to obtain degradation of the mRNA of the target gene.

  本发明提供了式（1）的核苷和包含至少一种式（2）核苷的寡核苷酸；发明的另一个方面涉及一种抑制细胞中基因表达的方法，该方法包括（a）将本发明的寡核苷酸与细胞接触；和（b）维持步骤（a）中的细胞足够长的时间以获得目标基因mRNA的降解。
• NON-NATURAL RIBONUCLEOTIDES, AND METHODS OF USE THEREOF
  申请人：Manoharan Muthiah

  公开号：US20110130440A1

  公开（公告）日：2011-06-02

  One aspect of the present invention relates to modified nucleosides and oligonucleotides comprising such modified nucleosides. Another aspect of the invention relates to a method of inhibiting the expression of a gene in call, the method comprising (a) contacting an oligonucleotide of the invention with the cell; and (b) maintaining the cell from step (a) for a time sufficient to obtain degradation of the mRNA of the target gene.

  本发明的一个方面涉及改性核苷和包含这种改性核苷的寡核苷酸。本发明的另一个方面涉及一种抑制细胞中基因表达的方法，该方法包括：（a）将本发明的寡核苷酸与细胞接触；以及（b）维持从步骤（a）开始的细胞足够长的时间，以获得目标基因的mRNA降解。
• Nucleic Acid Chemical Modifications
  申请人：Alnylam Pharmaceuticals Inc.

  公开号：EP2669290A1

  公开（公告）日：2013-12-04

  The present invention provides nucleosides of formula (1) and oligonucleotides comprising at least on nucleoside of formula (2): Another aspect of the invention relates to a method of inhibiting the expression of a gene in cell, the method comprising (a) contacting and oligonucleotide of the invention with the cell; and (b) maintaining the cell from step (a) for a time sufficient to obtain degradation of the mRNA of the target gene.

  本发明提供了式(1)的核苷和至少包含一种式(2)核苷的寡核苷酸：本发明的另一方面涉及一种抑制细胞中基因表达的方法，该方法包括(a)将本发明的寡核苷酸与细胞接触；(b)将步骤(a)中的细胞维持足够长的时间，使目的基因的mRNA降解。
• SOCHACKA, ELZBIETA;NAWROT, BARBARA;PANKIEWICZ, KRZYSZTOF W.;WATANABE, KYO+, J. MED. CHEM., 33,(1990) N, C. 1995-1999
  作者：SOCHACKA, ELZBIETA、NAWROT, BARBARA、PANKIEWICZ, KRZYSZTOF W.、WATANABE, KYO+

  DOI：——

  日期：——
• NUCLEIC ACID CHEMICAL MODIFICATIONS
  申请人：Alnylam Pharmaceuticals Inc.

  公开号：EP2403863B1

  公开（公告）日：2013-08-28