5-fluorocytidine hydrochloride | 4590-33-4

• 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: 5-fluorocytidine hydrochloride
• 英文别名: 5-Fluorcytidin；5-Fluorcytidinhydrochlorid；fl5Cyt-Ribf.HCl；4-amino-1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-fluoropyrimidin-2-one;hydrochloride
• CAS: 4590-33-4
• 化学式: C₉H₁₂FN₃O₅*ClH
• 分子量: 297.671
• InChiKey: QSCPWYVUCMTFAF-HCXTZZCQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.0
• 重原子数：
  19.0
• 可旋转键数：
  2.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  130.83
• 氢给体数：
  4.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  5-fluorocytidine hydrochloride 在 thionyl phosphate 、 三氯氧磷 作用下， 反应 5.0h， 生成 5-fluorocytidine monophosphate
  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