methyl 2,3,5-tri-O-(2,4-dichlorobenzyl)-D-ribofuranoside | 677299-16-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 2,3,5-tri-O-(2,4-dichlorobenzyl)-D-ribofuranoside
• 英文别名: (2R,3R,4R)-3,4-bis((2,4-dichlorobenzyl)oxy)-2-(((2,4-dichlorobenzyl)oxy)methyl)-5-methoxytetrahydrofuran；1-O-methyl-2,3,5-tris-O-(2,4-dichlorobenzyl)-D-ribofuranose；1-O-methyl-2,3,5-tri-O-(2,4-dichlorobenzyl)-D-riboside；D-Ribofuranoside, methyl 2,3,5-tris-O-[(2,4-dichlorophenyl)methyl]-；(2R,3R,4R)-3,4-bis[(2,4-dichlorophenyl)methoxy]-2-[(2,4-dichlorophenyl)methoxymethyl]-5-methoxyoxolane
• CAS: 677299-16-0
• 化学式: C₂₇H₂₄Cl₆O₅
• 分子量: 641.203
• InChiKey: QTZFDEIPDKCKBR-YGENNMJRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.9
• 重原子数：
  38
• 可旋转键数：
  11
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  46.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  methyl 2,3,5-tri-O-(2,4-dichlorobenzyl)-D-ribofuranoside 在 三氯异氰尿酸 、 四氯化锡 作用下， 以 二氯甲烷 为溶剂， 反应 6.17h， 生成 1-O-甲基-3,5-二-O-[(2,4-二氯苯基)甲基]-alpha-D-赤式戊呋喃糖苷-2-酮
  参考文献：
  名称：

  Discovery of 2′-α-C-Methyl-2′-β-C-fluorouridine Phosphoramidate Prodrugs as Inhibitors of Hepatitis C Virus

  摘要：

  2'-alpha-C-Methyl-2'-beta-C-fluorouridine and its phosphoramidate prodrugs were synthesized and evaluated for their inhibitory activity against HCV. The structure-activity relationship analysis of the phosphoramidate moiety found that 17m, 17q, and 17r exhibit potent activities against HCV, with EC50 values of 1.82 +/- 0.19, 0.88 +/- 0.12, and 2.24 +/- 0.22 mu M, respectively. The docking study revealed that the recognition of the 2'-beta-F by Arg158, 3'-OH by N291, and the Watson Crick pairing with the template allowed 23 to form the in-line conformation necessary for its incorporation into the viral RNA chain.

  DOI：

  10.1021/acsmedchemlett.6b00270
• 作为产物：
  描述：

  卡培他滨杂质25 在 18-冠醚-6 、 硫酸 、 potassium hydroxide 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 32.0h， 生成 methyl 2,3,5-tri-O-(2,4-dichlorobenzyl)-D-ribofuranoside
  参考文献：
  名称：

  [EN] NUCLEOSIDE-THIODIPHOSPHATE-HEPTOSE COMPOUNDS FOR TREATING CONDITIONS ASSOCIATED WITH ALPK1 ACTIVITY
  [FR] COMPOSÉS NUCLÉOSIDE-THIODIPHOSPHATE-HEPTOSE POUR TRAITER DES AFFECTIONS ASSOCIÉES À L'ACTIVITÉ DE L'ALPK1

  摘要：

  本发明涉及式(I)的化合物，该化合物调节，特别是激活α激酶1(ALPK1)，并且适用于治疗某种疾病、病症或障碍，其中ALPK1活性的降低或增加会导致该疾病、病症或障碍的病理学、症状或进展，例如癌症、免疫或炎症相关疾病。

  公开号：

  WO2022127914A1

文献信息

• 5-nitro-nucleoside compounds for treating viral infections
  申请人：Keicher D. Jesse

  公开号：US20060111311A1

  公开（公告）日：2006-05-25

  Disclosed are compounds, compositions and methods for treating viral infections caused by a flaviviridae family virus, such as hepatitis C virus.

  揭示了用于治疗由黄病毒科病毒引起的病毒感染的化合物、组合物和方法，例如丙型肝炎病毒。
• 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。
• NUCLEOSIDE DERIVATIVES FOR TREATING HEPATITIS C VIRUS INFECTION
  申请人：Roberts Christopher D.

  公开号：US20090036399A1

  公开（公告）日：2009-02-05

  Disclosed are methods for treating viral infections caused by a flaviviridae family virus, such as hepatitis C virus. Such compounds are represented by Formula I as follows: wherein W, W 1 , W 2 , Y, R 1 , Z, Y′ and R are as defined herein.

  本发明揭示了治疗由黄病毒科病毒引起的病毒感染的方法，例如丙型肝炎病毒。这些化合物的公式如下：其中W、W1、W2、Y、R1、Z、Y'和R的定义如下。
• NUCLEOSIDE COMPOUNDS FOR TREATING VIRAL INFECTIONS
  申请人：Roberts D. Christopher

  公开号：US20070167383A1

  公开（公告）日：2007-07-19

  Disclosed are compounds, compositions and methods for treating viral infections caused by a flaviviridae family virus, such as hepatitis C virus.

  本发明涉及用于治疗由黄病毒科病毒引起的病毒感染（例如丙型肝炎病毒）的化合物、组合物和方法。
• 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。