2',5'-di-O-acetyl-3'-deoxyuridine | 19312-45-9

• 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: 2',5'-di-O-acetyl-3'-deoxyuridine
• 英文别名: [(2S,4R,5R)-4-acetyloxy-5-(2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methyl acetate
• CAS: 19312-45-9
• 化学式: C₁₃H₁₆N₂O₇
• 分子量: 312.279
• InChiKey: TXWMDTGSEVKMJU-HOSYDEDBSA-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：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  111
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  2',5'-di-O-acetyl-3'-deoxyuridine 在 ammonium hydroxide 、 sodium ethanolate 、 2-氯苯基二氯膦 作用下， 以 1,4-二氧六环 、 吡啶 为溶剂， 反应 74.5h， 生成 3-脱氧胞苷
  参考文献：
  名称：

  Nucleosides. LVI¹Synthesis and Chemical Modifications of 3′-Deoxy-Pyrimidine Nucleosides

  摘要：

  3'-Deoxyuridine(1) and 3'-deoxycytidine(2) were prepared with improved yields by two different methods applying either the Barton procedure to appropriate 2',5'-di-O-protected pyrimidine nucleosides or by choosing the direct glycosylation of the pyrimidine bases with 1,2-di-O-acetyl-5-O-toluoyl-3-deoxy-D-erythro-pentofuranose via the silylation approach. Suitable protecting groups for the sugar moiety have been found in the trityl, tert-butyldimethylsilyl and the thexyl groups which are inert in the radical deoxygenation process. The newly synthesised compounds were characterised by elemental analyses and UV and H-1-NMR spectra.

  DOI：

  10.1080/15257779408012162
• 作为产物：
  描述：

  2',5'-di-O-acetyl-3-deoxy-N⁴-acetylcytidine 在 溶剂黄146 作用下， 以96%的产率得到2',5'-di-O-acetyl-3'-deoxyuridine
  参考文献：
  名称：

  Modified nucleosides for the treatment of viral infections and abnormal cellular proliferation

  摘要：

  所述的发明是关于一种用于在宿主中（包括动物，特别是人类）使用一般式（I）-（XXIII）的核苷或其药用可接受的盐或前药，对Flaviviridae（包括BVDV和HCV）、Orthomyxoviridae（包括流感A和B）或Paramyxoviridae（包括RSV）感染，或与异常细胞增殖相关的疾病进行座位的组合物和方法。该发明还提供了一种有效的过程，用于使用实时聚合酶链反应（“RT-PCR”）在宿主中定量病毒载量，特别是BVDV、HCV或西尼罗河病毒载量。此外，该发明还揭示了可以与样本中存在的病毒量成比例发出荧光的探针分子。

  公开号：

  US10100076B2

文献信息

• 一种3’-脱氧尿苷的制备方法
  申请人：上海兆维科技发展有限公司

  公开号：CN107033205B

  公开（公告）日：2020-05-19

  本发明涉及药物合成领域，具体是一种3’‑脱氧尿苷的制备方法，以化合物3为原料，先经乙酸酐保护氨基得到化合物4，再在乙酰溴作用下得到化合物5，经过次磷酸盐体系还原得到化合物6；在高压水蒸气与有机溶剂的作用下脱去脱乙酰氨基得化合物8或N‑乙酰基得化合物7，最后脱去全部乙酰基得到3’‑脱氧尿苷和3’‑脱氧胞苷的混合物，分离纯化分别得到3’‑脱氧尿苷和3’‑脱氧胞苷晶体；也可以由化合物6直接脱去全部乙酰基得到3’‑脱氧胞苷。本发明采用易得的天然产物为起始原料，操作简单，纯化方便，极易工业化大规模生产。
• Modified nucleosides for the treatment of viral infections and abnormal cellullar proliferation
  申请人：Stuyver Lieven

  公开号：US20110269707A1

  公开（公告）日：2011-11-03

  The disclosed invention is a composition for and a method of treating a Flaviviridae (including BVDV and HCV), Orthomyxoviridae (including Influenza A and B) or Paramyxoviridae (including RSV) infection, or conditions related to abnormal cellular proliferation, in a host, including animals, and especially humans, using a nucleoside of general formula (I)-(XXIII) or its pharmaceutically acceptable salt or prodrug. This invention also provides an effective process to quantify the viral load, and in particular BVDV, HCV or West Nile Virus load, in a host, using real-time polymerase chain reaction (“RT-PCR”). Additionally, the invention discloses probe molecules that can fluoresce proportionally to the amount of virus present in a sample.

  本公开发明涉及一种用于治疗Flaviviridae（包括BVDV和HCV）、Orthomyxoviridae（包括甲型和乙型流感）或Paramyxoviridae（包括RSV）感染或与异常细胞增殖相关的条件的组合物和方法，适用于宿主，包括动物，特别是人类，使用通式（I）-（XXIII）的核苷或其药学上可接受的盐或前药。本发明还提供了一种有效的过程，用于定量病毒载量，特别是BVDV、HCV或西尼罗河病毒载量，在宿主中使用实时聚合酶链反应（“RT-PCR”）。此外，本发明还揭示了探针分子，可以与样品中存在的病毒数量成比例地发出荧光。
• MODIFIED NUCLEOSIDES FOR THE TREATMENT OF VIRAL INFECTIONS AND ABNORMAL CELLULAR PROLIFERATION
  申请人：GILEAD SCIENCES, INC.

  公开号：US20140057863A1

  公开（公告）日：2014-02-27

  The disclosed invention is a composition for and a method of treating a Flaviviridae (including BVDV and HCV), Orthomyxoviridae (including Influenza A and B) or Paramyxoviridae (including RSV) infection, or conditions related to abnormal cellular proliferation, in a host, including animals, and especially humans, using a nucleoside of general formula (I)-(XXIII) or its pharmaceutically acceptable salt or prodrug. This invention also provides an effective process to quantify the viral load, and in particular BVDV, HCV or West Nile Virus load, in a host, using real-time polymerase chain reaction (“RT-PCR”). Additionally, the invention discloses probe molecules that can fluoresce proportionally to the amount of virus present in a sample.

  本公开发明涉及一种用于治疗Flaviviridae（包括BVDV和HCV）、Orthomyxoviridae（包括甲型和乙型流感病毒）或Paramyxoviridae（包括RSV）感染或与异常细胞增殖相关的条件的组合物和方法，适用于宿主，包括动物，特别是人类，使用一种核苷酸的一般式（I）-（XXIII）或其药学上可接受的盐或前药。本发明还提供了一种有效的过程，用于定量病毒载量，特别是BVDV、HCV或West Nile病毒载量，在宿主中使用实时聚合酶链反应（“RT-PCR”）。此外，本发明还揭示了可以与样品中存在的病毒数量成比例发光的探针分子。
• Synthesis of 5-haloethynyl- and 5-(1,2-dihalo)vinyluracil nucleosides: Antiviral activity and cellular toxicity
  作者：Vanessa Escuret、Vincent Aucagne、Nicolas Joubert、David Durantel、Kimberly L. Rapp、Raymond F. Schinazi、Fabien Zoulim、Luigi A. Agrofoglio

  DOI：10.1016/j.bmc.2005.06.021

  日期：2005.11

  In this article, we report the synthesis of hitherto unknown 5-haloethynyl and 5-(1,2-dihalo)vinyluracil nucleosides in the 2'-deoxy, 3'-deoxy- and ribosyl series, and we discuss their in vitro anti-HIV and anti-HCV activities and cellular toxicitites. As a result, on the basis of their selectivity index (SI) obtained with the HCV replicon system, but also on their cytotoxicity on peripheral blood mononuclear, CEM and VERO cell lines, the best compounds were the 5-bromoethynyluridine (SI = 3.2) and the 5-(1-chloro-2-iodo)vinyluridine (SI > 2.8). (c) 2005 Elsevier Ltd. All rights reserved.
• MODIFIED NUCLEOSIDES FOR TREATMENT OF VIRAL INFECTIONS AND ABNORMAL CELLULAR PROLIFERATION
  申请人：Pharmasset, Inc.

  公开号：EP1411954B1

  公开（公告）日：2010-12-15