2',5'-di-O-acetyl-3'-deoxy-5-ethynyluridine | 866836-92-2

• 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'-deoxy-5-ethynyluridine
• 英文别名: 1-(2,5-di-O-acetyl-3-deoxy-β-D-erythropentofuranosyl)-5-ethynyluracil；[(2S,4R,5R)-4-acetyloxy-5-(5-ethynyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methyl acetate
• CAS: 866836-92-2
• 化学式: C₁₅H₁₆N₂O₇
• 分子量: 336.301
• InChiKey: LYDLWAHWPJXGIA-OUCADQQQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.4
• 重原子数：
  24
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.47
• 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'-deoxy-5-ethynyluridine 在 吡啶 、 sodium hydroxide 、 2,6-二甲基吡啶高氯酸银 、 iodonium(di-γ-collidine) perchlorate 作用下， 以 乙醇 、 水 、 乙腈 为溶剂， 生成 5-(2-iodoethynyl)-3'-deoxyuridine
  参考文献：
  名称：

  Synthesis of 5-haloethynyl- and 5-(1,2-dihalo)vinyluracil nucleosides: Antiviral activity and cellular toxicity

  摘要：

  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.

  DOI：

  10.1016/j.bmc.2005.06.021
• 作为产物：
  描述：

  Acetic acid (2R,3R,5S)-5-acetoxymethyl-2-(2,4-dioxo-5-trimethylsilanylethynyl-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yl ester 在 四丁基氟化铵 作用下， 以 乙腈 为溶剂， 生成 2',5'-di-O-acetyl-3'-deoxy-5-ethynyluridine
  参考文献：
  名称：

  Synthesis of 5-haloethynyl- and 5-(1,2-dihalo)vinyluracil nucleosides: Antiviral activity and cellular toxicity

  摘要：

  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.

  DOI：

  10.1016/j.bmc.2005.06.021

文献信息

• Modified nucleosides for the treatment of viral infections and abnormal cellular proliferation
  申请人：——

  公开号：US20030087873A1

  公开（公告）日：2003-05-08

  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.

  该公开的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有关的病况的组合物和方法，适用于宿主，包括动物，尤其是人类，使用通用式（I）-（XXIII）的核苷或其药学上可接受的盐或前药。该发明还提供了一种有效的过程，用于量化病毒载量，特别是BVDV、HCV或西尼罗河病毒载量，使用实时聚合酶链反应（RT-PCR）。此外，该发明揭示了可以与样本中存在的病毒数量成比例发光的探针分子。
• Uridine derivatives as antiviral drugs against a flaviviridae, especially HCV
  申请人：INSTITUT NATIONAL DE LA SANTE ET DE LA RECHERCHE MEDICALE (INSERM)

  公开号：EP1674104A1

  公开（公告）日：2006-06-28

  The invention relates to the use of an uridine derivative of formula (I): wherein R1 represents monohalogenated alkynyl or dihalogenated alkenyl; R2 is chosen from among hydrogen, hydroxyl, -O-alkyl, -O-CO-alkyl and halogen; R3 is chosen from among hydrogen, hydroxyl, -O-alkyl, -O-CO-alkyl, halogen, -SH, -S-alkyl and N3; and R4 is chosen from among hydroxyl, -O-alkyl, -O-CO-alkyl, -O-phosphate, -O-diphosphate, -O-triphosphate and -O-phosphonate, as well as its possible tautomers, its possible pharmaceutically acceptable addition salts with an acid or a base, and its N-oxide forms, for the preparation of a drug having antiviral activity against a Flaviviridae.

  本发明涉及使用具有以下式（I）的尿苷衍生物： 其中 R1代表单卤代炔基或双卤代烯基； R2选择自氢、羟基、-O-烷基、-O-CO-烷基和卤素之一； R3选择自氢、羟基、-O-烷基、-O-CO-烷基、卤素、-SH、-S-烷基和N3之一； R4选择自羟基、-O-烷基、-O-CO-烷基、-O-磷酸酯、-O-二磷酸酯、-O-三磷酸酯和-O-膦酸酯之一， 以及其可能的互变异构体、其可能与酸或碱形成的药学上可接受的加合盐，以及其N-氧化物形式， 用于制备具有抗黄病毒活性的药物。
• Uridine Derivatives as Antiviral Drugs Against a Flaviviridae, Especially Hcv
  申请人：Aucagne Vincent

  公开号：US20090004137A1

  公开（公告）日：2009-01-01

  The invention relates to the use of an uridine derivative of formula (I); wherein —R 1 represents monohalogenated alkynyl or dihalogenated alkenyl; —R 2 is chosen from among hydrogen, hydroxyl, O-alkyl, O—CO alkyl and halogen; —R 3 is chosen from among hydrogen, hydroxyl, O-alkyl, O—CO alkyl, halogen, SH, S-alkyl and N 3 ; and —R 4 is chosen from among hydroxyl, O-alkyl, O—CO alkyl, O-phosphate, O-diphosphate, O-triphosphate and O phosphonate, as well as its possible tautomers, its possible pharmaceutically acceptable addition salts with an acid or a base, and its N-oxide forms, for the preparation of a drug having antiviral activity against a Flaviviridae.

  本发明涉及使用式（I）的尿嘧啶衍生物，其中—R1代表单卤代炔基或双卤代烯基；—R2选择自氢、羟基、O-烷基、O—CO烷基和卤素；—R3选择自氢、羟基、O-烷基、O—CO烷基、卤素、SH、S-烷基和N3；以及—R4选择自羟基、O-烷基、O—CO烷基、O-磷酸酯、O-二磷酸酯、O-三磷酸酯和O-膦酸酯，以及其可能的互变异构体、其可能的与酸或碱的药学上可接受的加盐物和其N-氧化物形式，用于制备具有抗Flaviviridae病毒活性的药物。
• 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。