5-fluorocytidine-5'-monophosphate diammonium salt | 94427-57-3

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘧啶核苷酸
• 英文名称: 5-fluorocytidine-5'-monophosphate diammonium salt
• CAS: 94427-57-3
• 化学式: C₉H₁₃FN₃O₈P*2H₃N
• 分子量: 375.251
• InChiKey: MWQLJBVFDAMSPJ-HCXTZZCQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.14
• 重原子数：
  23.0
• 可旋转键数：
  4.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  212.36
• 氢给体数：
  6.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  5-fluorocytidine-5'-monophosphate diammonium salt 在 吡啶 、 N,N'-二环己基-4-吗啉脒 、 2,2'-二硫二吡啶 、 三苯基膦 作用下， 反应 3.0h， 以27%的产率得到5-fluorocytidine cyclic 3',5'-monophosphate ammonium salt
  参考文献：
  名称：

  Synthesis and antitumor and antiviral activities of a series of 1-.beta.-D-ribofuranosyl-5-halocytosine (5-halocytidine) cyclic 3',5'-monophosphates

  摘要：

  A series of 1-beta-ribofuranosyl-5-halocytosine cyclic 3',5'-monophosphates (1-4) has been prepared. Direct halogenation of cytidine 3',5'-monophosphate (cCMP) yielded the Cl, Br, and I compounds while 5-F-cCMP (1) was obtained on cyclization of the 5'-monophosphate. On in vitro testing of 1-4 against L1210 and P388 leukemias, only 1 showed significant low-level activity (ID50 = 3.1 X 10(-4) mmol/L). Derivatives 2-4 were inactive at 10(-1) mmol/L and also proved to have low viral ratings against a series of RNA and DNA virus strains in vitro. By contrast the 5-F-cCMP showed moderate activity against VV, HSV-1, and HSV-2 strains (VR = 0.6-0.9). Both 5-fluorocytidine and 5-fluorocytidine 5'-monophosphate had marked antiviral activity (VR = 1.0-2.1) with the above viruses as well as with parainfluenza virus type 3. The nucleoside and nucleotide also were more active than 5-F-cCMP against L1210 and P388 cells. However, comparison of the cytotoxicities and antiviral ED50 values of 5-F-cCMP, 5-fluorocytidine 5'-monophosphate, and 5-fluorocytidine suggests a potential therapeutic advantage for 5-F-cCMP. Possible rationales for these activities are discussed in terms of 5-F-cCMP and the corresponding 5'-monophosphate as potential prodrugs and as sources, following enzymatic deamination, of cytotoxic 5-fluorouridine or its 5'-monophosphate.

  DOI：

  10.1021/jm00382a005
• 作为产物：
  描述：

  2',3',5'-Tri-O-acetyl-5-fluoruridin-5'-monophosphat 在 ammonium hydroxide 、 氨 作用下， 以 1,4-二氧六环 、 甲醇 为溶剂， 反应 1.0h， 生成 5-fluorocytidine-5'-monophosphate diammonium salt
  参考文献：
  名称：

  Krug, A.; Schmidt, S.; Lekschas, J., Journal fur praktische Chemie (Leipzig 1954), 1989, vol. 331, # 5, p. 835 - 842

  摘要：

  DOI：