1-(2'-O-methyl-β-D-ribofuranosyl)-5-nitroindole | 545374-63-8

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 吲哚核糖核苷和核糖核苷酸
• 英文名称: 1-(2'-O-methyl-β-D-ribofuranosyl)-5-nitroindole
• 英文别名: (2R,3R,4R,5R)-2-(hydroxymethyl)-4-methoxy-5-(5-nitroindol-1-yl)oxolan-3-ol
• CAS: 545374-63-8
• 化学式: C₁₄H₁₆N₂O₆
• 分子量: 308.291
• InChiKey: SKCRYKVHJCHUNQ-AAVRWANBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  110
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  1-(2'-O-methyl-β-D-ribofuranosyl)-5-nitroindole 在 N,N-二异丙基乙胺 作用下， 以 吡啶 、 二氯甲烷 为溶剂， 生成 Diisopropyl-phosphoramidous acid (2R,3R,4R,5R)-2-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-4-methoxy-5-(5-nitro-indol-1-yl)-tetrahydro-furan-3-yl ester 2-cyano-ethyl ester
  参考文献：
  名称：

  1-（2' - O-甲基-β-d-呋喃呋喃糖基）-5-硝基吲哚及其亚磷酰胺衍生物的合成

  摘要：

  描述了1-（2' - O-甲基-β-d-呋喃呋喃糖基）-5-硝基吲哚，含有通用碱基5-硝基吲哚的新核苷及其亚磷酰胺衍生物的合成，该衍生物用于掺入寡核苷酸。

  DOI：

  10.1016/j.tetlet.2004.05.116
• 作为产物：
  描述：

  2,3-O-isopropylidene-5-O-(tert-butyldimethylsilyl)-α-D-ribofuranosyl chloride 在 sodium hydride 、 triethylamine tris(hydrogen fluoride) 、 三氟乙酸 作用下， 以 四氢呋喃 、 吡啶 、 水 、 乙腈 为溶剂， 反应 3.0h， 生成 1-(2'-O-methyl-β-D-ribofuranosyl)-5-nitroindole
  参考文献：
  名称：

  1-（2' - O-甲基-β-d-呋喃呋喃糖基）-5-硝基吲哚及其亚磷酰胺衍生物的合成

  摘要：

  描述了1-（2' - O-甲基-β-d-呋喃呋喃糖基）-5-硝基吲哚，含有通用碱基5-硝基吲哚的新核苷及其亚磷酰胺衍生物的合成，该衍生物用于掺入寡核苷酸。

  DOI：

  10.1016/j.tetlet.2004.05.116

文献信息

• Oligonucleotides comprising a modified or non-natural nucleobase
  申请人：Manoharan Muthiah

  公开号：US20060035254A1

  公开（公告）日：2006-02-16

  One aspect of the present invention relates to a double-stranded oligonucleotide comprising at least one non-natural nucleobase. In certain embodiments, the non-natural nucleobase is difluorotolyl, nitroindolyl, nitropyrrolyl, or nitroimidazolyl. In a preferred embodiment, the non-natural nucleobase is difluorotolyl. In certain embodiments, only one of the two oligonucleotide strands comprising the double-stranded oligonucleotide contains a non-natural nucleobase. In certain embodiments, both of the oligonucleotide strands comprising the double-stranded oligonucleotide independently contain a non-natural nucleobase. In certain embodiments, the oligonucleotide strands comprise at least one modified sugar moiety. Another aspect of the present invention relates to a single-stranded oligonucleotide comprising at least one non-natural nucleobase. In a preferred embodiment, the non-natural nucleobase is difluorotolyl. In certain embodiments, the ribose sugar moiety that occurs naturally in nucleosides is replaced with a hexose sugar, polycyclic heteroalkyl ring, or cyclohexenyl group. In certain embodiments, at least one phosphate linkage in the oligonucleotide has been replaced with a phosphorothioate linkage.

  本发明的一个方面涉及含有至少一个非自然碱基的双链寡核苷酸。在某些实施例中，非自然碱基可以是二氟基甲苯基、硝基吲哚基、硝基吡咯基或硝基咪唑基。在一个首选实施例中，非自然碱基是二氟基甲苯基。在某些实施例中，双链寡核苷酸中的两个寡核苷酸链中只有一个含有非自然碱基。在某些实施例中，双链寡核苷酸中的两个寡核苷酸链都独立地含有非自然碱基。在某些实施例中，寡核苷酸链包含至少一个修饰的糖基。本发明的另一个方面涉及含有至少一个非自然碱基的单链寡核苷酸。在一个首选实施例中，非自然碱基是二氟基甲苯基。在某些实施例中，取代了核苷中天然存在的核糖糖基的是己糖糖基、多环杂烷基环或环己烯基团。在某些实施例中，寡核苷酸中的至少一个磷酸酯键被磷酸硫酯键取代。
• OLIGONUCLEOTIDES COMPRISING A MODIFIED OR NON-NATURAL NUCLEOBASE
  申请人：MANOHARAN Muthiah

  公开号：US20090281298A1

  公开（公告）日：2009-11-12

  One aspect of the present invention relates to a double-stranded oligonucleotide comprising at least one non-natural nucleobase. In certain embodiments, the non-natural nucleobase is difluorotolyl, nitroindolyl, nitropyrrolyl, or nitroimidazolyl. In a preferred embodiment, the non-natural nucleobase is difluorotolyl. In certain embodiments, only one of the two oligonucleotide strands comprising the double-stranded oligonucleotide contains a non-natural nucleobase. In certain embodiments, both of the oligonucleotide strands comprising the double-stranded oligonucleotide independently contain a non-natural nucleobase. In certain embodiments, the oligonucleotide strands comprise at least one modified sugar moiety. Another aspect of the present invention relates to a single-stranded oligonucleotide comprising at least one non-natural nucleobase. In a preferred embodiment, the non-natural nucleobase is difluorotolyl. In certain embodiments, the ribose sugar moiety that occurs naturally in nucleosides is replaced with a hexose sugar, polycyclic heteroalkyl ring, or cyclohexenyl group. In certain embodiments, at least one phosphate linkage in the oligonucleotide has been replaced with a phosphorothioate linkage.

  本发明的一个方面涉及至少包含一种非天然核碱基的双链寡核苷酸。在某些实施例中，非天然核碱基是二氟基甲苯基、硝基吲哚基、硝基吡咯基或硝基咪唑基。在一个首选实施例中，非天然核碱基是二氟基甲苯基。在某些实施例中，仅有双链寡核苷酸中的两个寡核苷酸链中的一个包含非天然核碱基。在某些实施例中，包含双链寡核苷酸的两个寡核苷酸链独立地包含非天然核碱基。在某些实施例中，寡核苷酸链包括至少一个修饰的糖基团。本发明的另一个方面涉及至少包含一种非天然核碱基的单链寡核苷酸。在一个首选实施例中，非天然核碱基是二氟基甲苯基。在某些实施例中，核苷中天然存在的核苷糖被替换为六碳糖、多环杂基烷基环或环己烯基团。在某些实施例中，寡核苷酸中的至少一个磷酸酯连接被替换为磷酸硫酯连接。
• Oligonucleotides comprising a ligand tethered to a modified or non-natural nucleobase
  申请人：Manoharan Muthiah

  公开号：US20070054279A1

  公开（公告）日：2007-03-08

  One aspect of the present invention relates to a double-stranded oligonucleotide comprising at least one ligand tethered to an altered or non-natural nucleobase. In certain embodiments, the non-natural nucleobase is difluorotolyl, nitropyrrolyl, or nitroimidazolyl. In certain embodiments, the ligand is a steroid or aromatic compound. In certain embodiments, only one of the two oligonucleotide strands comprising the double-stranded oligonucleotide contains a ligand tethered to an altered or non-natural nucleobase. In certain embodiments, both of the oligonucleotide strands comprising the double-stranded oligonucleotide independently contain a ligand tethered to an altered or non-natural nucleobase. In certain embodiments, the oligonucleotide strands comprise at least one modified sugar moiety. Another aspect of the present invention relates to a single-stranded oligonucleotide comprising at least one ligand tethered to an altered or non-natural nucleobase. In certain embodiments, the non-natural nucleobase is difluorotolyl, nitropyrrolyl, or nitroimidazolyl. In certain embodiments, the ligand is a steroid or aromatic compound. In certain embodiments, the ribose sugar moiety that occurs naturally in nucleosides is replaced with a hexose sugar, polycyclic heteroalkyl ring, or cyclohexenyl group. In certain embodiments, at least one phosphate linkage in the oligonucleotide has been replaced with a phosphorothioate linkage.

  本发明的一个方面涉及一种双链寡核苷酸，其中至少一个配体被系在改变或非天然核碱基上。在某些实施例中，非天然核碱基是二氟基甲苯基、硝基吡咯基或硝基咪唑基。在某些实施例中，配体是类固醇或芳香化合物。在某些实施例中，只有双链寡核苷酸中的两个寡核苷酸链之一包含系在改变或非天然核碱基上的配体。在某些实施例中，双链寡核苷酸中的两个寡核苷酸链都独立地包含系在改变或非天然核碱基上的配体。在某些实施例中，寡核苷酸链包括至少一个修饰糖基。本发明的另一个方面涉及一种单链寡核苷酸，其中至少一个配体被系在改变或非天然核碱基上。在某些实施例中，非天然核碱基是二氟基甲苯基、硝基吡咯基或硝基咪唑基。在某些实施例中，配体是类固醇或芳香化合物。在某些实施例中，核苷酸中自然存在的核苷糖被替换为六糖、多环杂基烷基环或环己烯基团。在某些实施例中，寡核苷酸中至少一个磷酸酯键被磷酸硫酯键所替代。
• OLIGNUCLEOTIDES COMPRISING A LIGAND TETHERED TO A MODIFIED OR NON-NATURAL NUCLEOBASE
  申请人：MANOHARAN Muthiah

  公开号：US20090312531A1

  公开（公告）日：2009-12-17

  One aspect of the present invention relates to a double-stranded oligonucleotide comprising at least one ligand tethered to an altered or non-natural nucleobase. In certain embodiments, the non-natural nucleobase is difluorotolyl, nitropyrrolyl, or nitroimidazolyl. In certain embodiments, the ligand is a steroid or aromatic compound. In certain embodiments, only one of the two oligonucleotide strands comprising the double-stranded oligonucleotide contains a ligand tethered to an altered or non-natural nucleobase. In certain embodiments, both of the oligonucleotide strands comprising the double-stranded oligonucleotide independently contain a ligand tethered to an altered or non-natural nucleobase. In certain embodiments, the oligonucleotide strands comprise at least one modified sugar moiety. Another aspect of the present invention relates to a single-stranded oligonucleotide comprising at least one ligand tethered to an altered or non-natural nucleobase. In certain embodiments, the non-natural nucleobase is difluorotolyl, nitropyrrolyl, or nitroimidazolyl. In certain embodiments, the ligand is a steroid or aromatic compound. In certain embodiments, the ribose sugar moiety that occurs naturally in nucleosides is replaced with a hexose sugar, polycyclic heteroalkyl ring, or cyclohexenyl group. In certain embodiments, at least one phosphate linkage in the oligonucleotide has been replaced with a phosphorothioate linkage.

  本发明的一个方面涉及一种双链寡核苷酸，其中至少有一种配体被系着到改变或非自然的核碱基上。在某些实施例中，非自然的核碱基是二氟基甲苯基、硝基吡咯基或硝基咪唑基。在某些实施例中，配体是类固醇或芳香族化合物。在某些实施例中，只有双链寡核苷酸中的两条寡核苷酸链中的一条包含系着到改变或非自然核碱基上的配体。在某些实施例中，双链寡核苷酸中的两条寡核苷酸链都独立地包含系着到改变或非自然核碱基上的配体。在某些实施例中，寡核苷酸链包含至少一个改变的糖基团。本发明的另一个方面涉及一种单链寡核苷酸，其中至少有一种配体被系着到改变或非自然的核碱基上。在某些实施例中，非自然的核碱基是二氟基甲苯基、硝基吡咯基或硝基咪唑基。在某些实施例中，配体是类固醇或芳香族化合物。在某些实施例中，自然存在于核苷中的核糖糖基团被替换为六碳糖、多环杂环烷基环或环己烯基团。在某些实施例中，寡核苷酸中至少有一个磷酸酯键被磷酸硫酯键替换。
• RNAI inhibition of influenza virus replication
  申请人：Alnylam Pharmaceuticals Inc.

  公开号：EP2202239A1

  公开（公告）日：2010-06-30

  The invention relates to compositions and methods for modulating the expression of influenza viral genes, and more particularly to the downregulation of influenza viral genes by chemically modified oligonucleotides.

  本发明涉及调节流感病毒基因表达的组合物和方法，特别是通过化学修饰寡核苷酸下调流感病毒基因的组合物和方法。