3'-phospho-5'-DFUR | 1367788-07-5

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 核糖核苷3'-磷酸盐
• 英文名称: 3'-phospho-5'-DFUR
• 英文别名: [(2R,3S,4R,5R)-5-(5-fluoro-2,4-dioxopyrimidin-1-yl)-4-hydroxy-2-methyloxolan-3-yl] dihydrogen phosphate
• CAS: 1367788-07-5
• 化学式: C₉H₁₂FN₂O₈P
• 分子量: 326.175
• InChiKey: CLVWLRWPLVKOSN-ZIYNGMLESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.6
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  146
• 氢给体数：
  4
• 氢受体数：
  9

反应信息

• 作为产物：
  描述：

  去氧氟尿苷 在 Sodium trimetaphosphate 、 sodium hydroxide 、 盐酸 、 水 作用下， 以 水 为溶剂， 反应 456.0h， 生成 3'-phospho-5'-DFUR 、 2'-phospho-5'-DFUR
  参考文献：
  名称：

  Phosphorylation of 5'-Deoxy-5-fluorouridine with Inorganic Phosphorylating Agents

  摘要：

  无机环三聚磷酸（P3m，Na3P3O9）和单亚胺环三聚磷酸（MCTP，Na3P3O8NH）在水溶液中实现了 5′-脱氧-5-氟尿苷（多西氟脲，5′-DFUR）的磷酸化。在 5′-DFUR 与 P3m 的反应中，合成了 2′-单磷酸-5′-DFUR 和 3′-单磷酸-5′-DFUR，总产率超过 95%。在 5′-DFUR 与 MCTP 的反应中，合成了 2′-二磷酰胺基膦酰基-5′-DFUR 和 3′-二磷酰胺基膦酰基-5′-DFUR，总产率超过 40%。P3m 和 MCTP 磷酸化产物在中性和碱性溶液中都很稳定。

  DOI：

  10.1248/cpb.59.1447

文献信息

• METHODS AND COMPOSITIONS FOR TREATING OR AMELIORATING CANCER USING GEMCITABINE-5'-ELAIDATE
  申请人：Clavis Pharma ASA

  公开号：EP2552453A2

  公开（公告）日：2013-02-06
• Methods and Compositions for Treating or Ameliorating Cancer Using Gemcitabine-5'-Elaidate
  申请人：Sandvold Marit Liland

  公开号：US20130005678A1

  公开（公告）日：2013-01-03

  This invention provides methods and compositions for treating or otherwise ameliorating cancer in a subject, along with methods and compositions for measuring the levels of nucleoside transporters in a tumor and correlating this level to a predicated efficacy of a given anti-cancer drug regime, and methods and compositions for treating patients with low levels of hENT1 expression in cancer cells using a lipophilic gemcitabine analog such as gemcitabine-5′-elaidate.
• [EN] PHARMACEUTICALLY ACTIVE LIPID-BASED FORMULATION OF NUCLEOSIDE-LIPID CONJUGATES<br/>[FR] COMPOSITIONS PHARMACEUTIQUEMENT ACTIVES A BASE DE LIPIDES, DE CONJUGUES NUCLEOSIDES-LIPIDES
  申请人：NEOPHARM INC

  公开号：WO2006102533A2

  公开（公告）日：2006-09-28

  [EN] Novel formulations of nucleoside-lipid conjugates, the methods of preparing them and the methods for administering them are provided. More particularly, methods for making liposomal formulations of nucleoside-cardiolipin and analogues thereof are provided. By encapsulating nucleoside prodrugs, drugs are protected from degradation, thereby extending the drugs' plasma half-life and intracellular release. In addition, compositions that demonstrate greater efficacy and higher cytotoxicity are produced. Accordingly, nucleoside-lipid conjugates that demonstrate greater in-vitro and in-vivo activity are produced.
  [FR] Nouvelles compositions de conjugués nucléosides-lipides, méthodes de préparation desdits conjugués et méthodes d'administration desdites compositions. Plus particulièrement, la présente invention concerne des méthode de préparation de compositions liposomales de nucléosides-cardiolipine et d'analogues desdites substances. L'encapsulation des promédicaments à base de nucléosides protège ces médicaments de la dégradation, ce qui prolonge la demi-vie du médicament dans le plasma et la libération intracellulaire. De plus, la présente invention concerne des compositions qui présentent une plus grande efficacité et une plus grande cytotoxicité. Par conséquent, lesdits conjugués nucléosides-lipides produits selon la présente invention présentent une activité accrue in vitro et in vivo.
• [EN] METHODS AND COMPOSITIONS FOR TREATING OR AMELIORATING CANCER USING GEMCITABINE-5'-ELAIDATE<br/>[FR] PROCÉDÉS D'AMÉLIORATION DU CANCER
  申请人：CLAVIS PHARMA ASA

  公开号：WO2011121453A2

  公开（公告）日：2011-10-06

  This invention provides methods and compositions for treating or otherwise ameliorating cancer in a subject, along with methods and compositions for measuring the levels of nucleoside transporters in a tumor and correlating this level to a predicated efficacy of a given anti-cancer drug regime, and methods and compositions for treating patients with low levels of hENTI expression in cancer cells using a lipophilic gemcitabine analog such as gemcitabine-5'-elaidate.
• Phosphorylation of 5'-Deoxy-5-fluorouridine with Inorganic Phosphorylating Agents
  作者：Hideko Maeda、Takuma Kusuhara、Mitsutomo Tsuhako、Hirokazu Nakayama

  DOI：10.1248/cpb.59.1447

  日期：——

  The phosphorylation of 5′-deoxy-5-fluorouridine (doxifluridine, 5′-DFUR) has been achieved using inorganic cyclo-triphosphate (P3m, Na3P3O9) and monoimido-cyclo-triphosphate (MCTP, Na3P3O8NH) in aqueous solution. In the reaction of 5′-DFUR with P3m, 2′-monophospho-5′-DFUR and 3′-monophospho-5′-DFUR were synthesized with a total yield of more than 95%. In the reaction of 5′-DFUR with MCTP, 2′-diphosphoramidophosphono-5′-DFUR and 3′-diphosphoramidophosphono-5′-DFUR were synthesized with a total yield of more than 40%. The phosphorylated products with P3m and MCTP were stable in neutral and alkaline solutions.

  无机环三聚磷酸（P3m，Na3P3O9）和单亚胺环三聚磷酸（MCTP，Na3P3O8NH）在水溶液中实现了 5′-脱氧-5-氟尿苷（多西氟脲，5′-DFUR）的磷酸化。在 5′-DFUR 与 P3m 的反应中，合成了 2′-单磷酸-5′-DFUR 和 3′-单磷酸-5′-DFUR，总产率超过 95%。在 5′-DFUR 与 MCTP 的反应中，合成了 2′-二磷酰胺基膦酰基-5′-DFUR 和 3′-二磷酰胺基膦酰基-5′-DFUR，总产率超过 40%。P3m 和 MCTP 磷酸化产物在中性和碱性溶液中都很稳定。