1-(2-deoxy-2,2-difluoro-β-D-ribofuranosyl)-5-bromo-2,4-dioxo-1,2,3,4-tetrahydropyrimidine | 132786-35-7

• 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: 1-(2-deoxy-2,2-difluoro-β-D-ribofuranosyl)-5-bromo-2,4-dioxo-1,2,3,4-tetrahydropyrimidine
• 英文别名: 1-(2-deoxy-2,2-difluoro-β-D-erythro-pentofuranos-1-yl)-5-bromouracil；5-bromo-1-[(2R,4R,5R)-3,3-difluoro-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]pyrimidine-2,4-dione
• CAS: 132786-35-7
• 化学式: C₉H₉BrF₂N₂O₅
• 分子量: 343.082
• InChiKey: ZBQKEEPEYPQFAF-WYDQCIBASA-N

物化性质

• 密度：
  2.03±0.1 g/cm3(Predicted)
• 溶解度：
  可溶于DMF、乙酸乙酯、甲醇

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  99.1
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  1-(2-deoxy-2,2-difluoro-β-D-ribofuranosyl)-5-bromo-2,4-dioxo-1,2,3,4-tetrahydropyrimidine 、 phenyl(benzyloxy-L-alaninyl)phosphorochloridate 在 N-甲基咪唑 作用下， 以 四氢呋喃 为溶剂， 反应 24.0h， 以7%的产率得到benzyl (2S)-2-[[[(2R,3R,5R)-5-(5-bromo-2,4-dioxo-pyrimidin-1-yl)-4,4-difluoro-3-hydroxy-tetrahydrofuran-2-yl]methoxy-phenoxy-phosphoryl]amino]propanoate
  参考文献：
  名称：

  Design, synthesis and biological evaluation of 2′-deoxy-2′,2′-difluoro-5-halouridine phosphoramidate ProTides

  摘要：

  We report the synthesis of a series of novel 2'-deoxy-2',2'-difluoro-5-halouridines and their corresponding phosphoramidate ProTides. All compounds were evaluated for antiviral activity and for cellular toxicity. Interestingly, 2'-deoxy-2',2'-difluoro-5-iodo- and -5-bromo-uridines showed selective activity against feline herpes virus replication in cell culture due to a specific recognition (activation) by the virus-encoded thymidine kinase. Crown Copyright (C) 2011 Published by Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.05.037
• 作为产物：
  描述：

  2-脱氧-2,2-二氟戊呋喃糖-1-酮 3,5-二安息香酸盐 在 三氟甲磺酸三甲基硅酯 、 sodium methylate 、 lithium tri-t-butoxyaluminum hydride 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 1,1-二氯乙烷 、 二氯甲烷 为溶剂， 反应 29.0h， 生成 1-(2-deoxy-2,2-difluoro-β-D-ribofuranosyl)-5-bromo-2,4-dioxo-1,2,3,4-tetrahydropyrimidine
  参考文献：
  名称：

  Design, synthesis and biological evaluation of 2′-deoxy-2′,2′-difluoro-5-halouridine phosphoramidate ProTides

  摘要：

  We report the synthesis of a series of novel 2'-deoxy-2',2'-difluoro-5-halouridines and their corresponding phosphoramidate ProTides. All compounds were evaluated for antiviral activity and for cellular toxicity. Interestingly, 2'-deoxy-2',2'-difluoro-5-iodo- and -5-bromo-uridines showed selective activity against feline herpes virus replication in cell culture due to a specific recognition (activation) by the virus-encoded thymidine kinase. Crown Copyright (C) 2011 Published by Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.05.037

文献信息

• Pyrimidine Nucleosides Syntheses by Late-Stage Base Heterocyclization Reactions
  作者：Elfie S. Cavalli、Thomas Mies、Henry S. Rzepa、Andrew J. P. White、Philip J. Parsons、Anthony G.M. Barrett

  DOI：10.1021/acs.orglett.2c03152

  日期：2022.12.16

  An efficient two-step procedure for the syntheses of pyrimidine nucleosides is presented. A series of glycosyl 5-(aminomethylene)-1,3-dioxane-4,6-dione derivatives were prepared from β-anomeric isonitriles by reaction with Meldrum’s acid or by allowing aminomethylene Meldrum’s acid to react with an 1-aldofuranosyl halide or acetate. The resultant 5-(aminomethylene)-1,3-dioxane-4,6-dione derivatives

  提出了一种合成嘧啶核苷的有效两步法。一系列糖基 5-(氨基亚甲基)-1,3-二恶烷-4,6-二酮衍生物通过与 Meldrum 酸反应或通过使氨基亚甲基 Meldrum 酸与 1-醛糖呋喃基卤化物或乙酸盐反应，从 β-异头异腈制备. 生成的 5-(aminomethylene)-1,3-dioxane-4,6-dione 衍生物通过转酰基反应与异氰酸苄基或 2,4-二甲氧基苄基酯反应，得到 uridine-5-carboxylic acid 衍生物和相关核苷。这些核苷羧酸通过用N-溴代琥珀酰亚胺进行溴代脱羧而转化为其他 C-5 衍生物。
• Design, synthesis and biological evaluation of 2′-deoxy-2′,2′-difluoro-5-halouridine phosphoramidate ProTides
  作者：Maurizio Quintiliani、Leentje Persoons、Nicola Solaroli、Anna Karlsson、Graciela Andrei、Robert Snoeck、Jan Balzarini、Christopher McGuigan

  DOI：10.1016/j.bmc.2011.05.037

  日期：2011.7

  We report the synthesis of a series of novel 2'-deoxy-2',2'-difluoro-5-halouridines and their corresponding phosphoramidate ProTides. All compounds were evaluated for antiviral activity and for cellular toxicity. Interestingly, 2'-deoxy-2',2'-difluoro-5-iodo- and -5-bromo-uridines showed selective activity against feline herpes virus replication in cell culture due to a specific recognition (activation) by the virus-encoded thymidine kinase. Crown Copyright (C) 2011 Published by Elsevier Ltd. All rights reserved.