5-chlorocytidine cyclic 3',5'-monophosphate | 94427-53-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 5-chlorocytidine cyclic 3',5'-monophosphate
• 英文别名: 1-[(4aR,6R,7R,7aS)-2,7-dihydroxy-2-oxo-4a,6,7,7a-tetrahydro-4H-furo[3,2-d][1,3,2]dioxaphosphinin-6-yl]-4-amino-5-chloropyrimidin-2-one
• CAS: 94427-53-9
• 化学式: C₉H₁₁ClN₃O₇P
• 分子量: 339.629
• InChiKey: AFPXPOIWLTZAAD-UAKXSSHOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.4
• 重原子数：
  21
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  144
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  胞苷-3’,5’-环一磷酸 在 N,N'-二环己基-4-吗啉脒 、 N-氯代丁二酰亚胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 以34%的产率得到5-chlorocytidine cyclic 3',5'-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