(E)-5-(1,2-dibromovinyl)uridine

• 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: (E)-5-(1,2-dibromovinyl)uridine
• 英文别名: 5-[(E)-1,2-dibromoethenyl]-1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]pyrimidine-2,4-dione
• 化学式: C₁₁H₁₂Br₂N₂O₆
• 分子量: 428.034
• InChiKey: IAGYHBQPNFGKRP-VUEMSXQMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.4
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  119
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  2',3',5'-三乙酰尿苷 在 bis-triphenylphosphine-palladium(II) chloride 吡啶 、 sodium hydroxide 、 copper(l) iodide 、 ammonium cerium(IV) nitrate 、 四丁基氟化铵 、 溴 、 碘 、 三乙胺 作用下， 以 乙醇 、 水 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 生成 (E)-5-(1,2-dibromovinyl)uridine
  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

• 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。
• 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.