5-溴-1-(2-脱氧-2-氟-beta-D-阿拉伯呋喃糖基)-2,4(1H,3H)-嘧啶二酮 | 69123-97-3

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘧啶核苷
• 中文名称: 5-溴-1-(2-脱氧-2-氟-beta-D-阿拉伯呋喃糖基)-2,4(1H,3H)-嘧啶二酮
• 英文名称: 1-(2-deoxy-2-fluoro-β-D-arabinofuranosyl)-5-bromouracil
• 英文别名: 5-bromo-1-(2-fluoro-β-D-2-deoxy-arabinofuranosyl)-1H-pyrimidine-2,4-dione；5-bromo-1-[(2R,3S,4R,5R)-3-fluoro-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]pyrimidine-2,4-dione
• CAS: 69123-97-3
• 化学式: C₉H₁₀BrFN₂O₅
• 分子量: 325.091
• InChiKey: WFOXFPXBLFRFHB-BYPJNBLXSA-N

物化性质

• 密度：
  1.98±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.2
• 重原子数：
  18
• 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：
  6

反应信息

• 作为产物：
  描述：

  1-(O³-acetyl-O⁵-benzoyl-2-fluoro-β-D-2-deoxy-arabinofuranosyl)-1H-pyrimidine-2,4-dione 在 溴 、 sodium acetate 作用下， 以 methanolic ammonia 、 溶剂黄146 为溶剂， 生成 5-溴-1-(2-脱氧-2-氟-beta-D-阿拉伯呋喃糖基)-2,4(1H,3H)-嘧啶二酮
  参考文献：
  名称：

  Anti-herpes virus compositions containing 5-substituted

  摘要：

  动物用于治疗疱疹病毒的兽医学成分，包括嘧啶核苷或其兽医学上可接受的酸盐加成物，其化学式为##STR1##其中A为OR.sup.3，SR.sup.3，NR.sup.3R.sup.4或NHacyl，其中R.sup.3和R.sup.4相同或不同，为氢，1-7个碳原子的低级烷基，芳基烷基或芳基；NHacyl为烷酰基或芳酰胺基；B为氧或硫；X为卤素，烷基磺酰基或芳基磺酰基；Y为卤素，氨基，单烷基或单芳基氨基，二烷基氨基，氨甲基，羟甲基，低级烷基，芳基，芳基烷基，乙烯基和取代乙烯基或乙炔基和取代乙炔基；Z为亚甲基或氮；R.sup.1和R.sup.2相同或不同，为氢，酰基或芳酰基，在兽医学上可接受的载体中。

  公开号：

  US04594339A1

文献信息

• 5-Substituted
  申请人：Sloan Kettering Institute for Cancer Research

  公开号：US04211773A1

  公开（公告）日：1980-07-08

  Pyrimidine nucleosides exhibiting anti-viral and anti-tumor effects have the formula ##STR1## wherein A is OR.sup.3, SR.sup.3, NR.sup.3 R.sup.4 or NHacyl wherein R.sup.3 and R.sup.4 are the same or different and are hydrogen, lower alkyl of 1 to 7 carbon atoms, aralkyl, or aryl; NHacyl is alkanoyl or aroyl amide; B is oxygen or sulfur; X is halogen, alkylsulfonyl or arylsulfonyl; Y is halogen, amino, monoalkyl- or monoaralkylamino, dialkylamino, aminomethyl, hydroxymethyl, lower alkyl, aryl, aralkyl, vinyl and substituted vinyl or ethynyl and substituted ethynyl; Z is methyne or nitrogen; R.sup.1 and R.sup.2 are the same or different and are hydrogen acyl or aroyl.

  具有抗病毒和抗肿瘤效果的嘧啶核苷具有以下公式：##STR1## 其中A为OR.sup.3，SR.sup.3，NR.sup.3 R.sup.4或NHacyl，其中R.sup.3和R.sup.4相同或不同，为氢，1至7个碳原子的低级烷基，芳基烷基或芳基；NHacyl为烷酰基或芳酰基酰胺；B为氧或硫；X为卤素，烷基磺酰基或芳基磺酰基；Y为卤素，氨基，单烷基或单芳基氨基，双烷基氨基，氨甲基，羟甲基，低级烷基，芳基，芳基烷基，乙烯基和取代乙烯基或乙炔基和取代乙炔基；Z为亚甲基或氮；R.sup.1和R.sup.2相同或不同，为氢，酰基或芳酰基。
• 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。
• 5-Substituted 1-(2'-deoxy-2'-substituted-beta-D-arabinofuranosyl) pyrimidine nucleosides and pharmaceutical compositions containing them
  申请人：Sloan-Kettering Institute For Cancer Research

  公开号：EP0010205A1

  公开（公告）日：1980-04-30

  1. Pyrimidine nucleosides exhibiting anti-viral and anti-tumor effects have the formula wherein A is OR', SR', NR3R4 or NHacyl wherein R' and R' are the same or different and are hydrogen, lower alkyl of 1 to 7 carbon atoms, aralkyl, or aryl; NHacyl is alkanoyl or aroyl amide; B is oxygen or sulfur; X is halogen, alkylsulfonyl or arylsulfonyl; Y is halogen, amino, monoalkyl- or monoaralkylamino, dialkylamino, aminomethyl, hydroxymethyl, lower alkyl, aryl, aralkyl, vinyl and substituted vinyl or ethynyl and substituted ethynyl; Z is methyne or nitrogen; R1 and R2 are the same or different and are hydrogen acyl or aroyl.

  1.具有抗病毒和抗肿瘤作用的嘧啶核苷的化学式为 其中 A是OR'、SR'、NR3R4或NHacyl，其中R'和R'相同或不同，并且是氢、1至7个碳原子的低级烷基、芳基或芳基； NHacyl 是烷酰基或芳基酰胺； B 是氧或硫； X 是卤素、烷基磺酰基或芳基磺酰基； Y 是卤素、氨基、单烷基或单芳基氨基、二烷基氨基、氨甲基、羟甲基、低级烷基、芳基、芳烷基、乙烯基和取代乙烯基或乙炔基和取代乙炔基； Z 是甲基或氮； R1 和 R2 相同或不同，并且是氢酰基或芳基。
• SYNTHESIS OF 2'-DEOXY-2'-[18F]FLUORO-5-METHYL-1-B-D-ARABINOFURANOSYLURACIL (18F-FMAU)
  申请人：University of Southern California

  公开号：EP2603516B1

  公开（公告）日：2017-08-23
• SYNTHESIS OF 2'-Deoxy-2'-[18F]FLUORO-5-METHYL-1-B-D-ARABINOFURANOSYLURACIL (18F-FMAU)
  申请人：Li Zibo

  公开号：US20120053337A1

  公开（公告）日：2012-03-01

  The present invention relates to methods of synthesizing 18 F-FMAU. In particular, 18 F-FMAU is synthesized using one-pot reaction conditions in the presence of Friedel-Crafts catalysts. The one-pot reaction conditions are incorporated into a fully automated cGMP-compliant radiosynthesis module, which results in a reduction in synthesis time and simplifies reaction conditions. The one-pot reaction conditions are also suitable for the production of 5-substitued thymidine or cytidine analogues. The products from the one-pot reaction (e.g. the labeled thymidine or cytidine analogues) can be used as probes for imaging tumor proliferative activity. More specifically, these [ 18 F]-labeled thymidine or cytidine analogues can be used as a PET tracer for certain medical conditions, including, but not limited to, cancer disease, autoimmunity inflammation, and bone marrow transplant.