1-(2-脱氧-2-氟-beta-D-阿拉伯呋喃糖基)-5-溴胞嘧啶 | 69123-93-9

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘧啶核苷
• 中文名称: 1-(2-脱氧-2-氟-beta-D-阿拉伯呋喃糖基)-5-溴胞嘧啶
• 英文名称: 4-amino-5-bromo-1-(2-fluoro-β-D-2-deoxy-arabinofuranosyl)-1H-pyrimidin-2-one
• 英文别名: 1-(2-deoxy-2-fluoro-β-D-arabinofuranosyl)-5-bromocytosine；2'-Fluoro-5-bromo-1-beta-D-arabinofuranosylcytosine；4-amino-5-bromo-1-[(2R,3S,4R,5R)-3-fluoro-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]pyrimidin-2-one
• CAS: 69123-93-9
• 化学式: C₉H₁₁BrFN₃O₄
• 分子量: 324.106
• InChiKey: DPTQLSGNVUCAMZ-BYPJNBLXSA-N

物化性质

• 沸点：
  513.3±60.0 °C(Predicted)
• 密度：
  2.21±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.5
• 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：
  108
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  1-(O³-acetyl-O⁵-benzoyl-2-fluoro-β-D-2-deoxy-arabinofuranosyl)-4-amino-5-bromo-1H-pyrimidin-2-one 在 乙醇 作用下， 以 氨 为溶剂， 反应 24.0h， 以to give 560 mg of 1-(2-deoxy-2-fluoro-β-D-arabinofuranosyl)-5-bromocytosine, m.p. 201°-202°的产率得到1-(2-脱氧-2-氟-beta-D-阿拉伯呋喃糖基)-5-溴胞嘧啶
  参考文献：
  名称：

  5-Substituted

  摘要：

  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，是氢，1到7个碳原子的低级烷基，芳基烷基或芳基；NHacyl为脂肪酰基或芳酰基酰胺；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，芳基烷基，乙烯基和取代乙烯基或乙炔基和取代乙炔基；Z是亚甲基或氮；R.sup.1和R.sup.2相同或不同，是氢，酰基或芳酰基。

  公开号：

  US04211773A1

文献信息

• Anti-herpes virus compositions containing 5-substituted
  申请人：Sloan-Kettering Institute for Cancer Research

  公开号：US04594339A1

  公开（公告）日：1986-06-10

  Veterinarian composition for the treatment of herpes virus in animals comprising a pyrimidine nucleoside, or veterinarianically acceptable acid addition salte thereof, of 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, in a veterinarianically acceptable carrier.

  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。
• 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：EP0010205B1

  公开（公告）日：1983-05-04
• 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.
• US4211773A
  申请人：——

  公开号：US4211773A

  公开（公告）日：1980-07-08