5-fluoro-2'-deoxyuridyl-(3'-5')-3'-C-ethynylcytidine tetrabutylammonium salt | 1070182-80-7

• 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: 5-fluoro-2'-deoxyuridyl-(3'-5')-3'-C-ethynylcytidine tetrabutylammonium salt
• CAS: 1070182-80-7
• 化学式: C₁₆H₃₆N*C₂₀H₂₂FN₅O₁₂P
• 分子量: 816.862
• InChiKey: XESUYCBJZDABFL-VWQZPSOQSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  1.29
• 重原子数：
  56.0
• 可旋转键数：
  20.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.72
• 拓扑面积：
  253.51
• 氢给体数：
  5.0
• 氢受体数：
  16.0

反应信息

• 作为产物：
  描述：

  、 四丁基氟化铵 、 水 以 四氢呋喃 为溶剂， 反应 72.0h， 以10.6 g的产率得到5-fluoro-2'-deoxyuridyl-(3'-5')-3'-C-ethynylcytidine tetrabutylammonium salt
  参考文献：
  名称：

  Synthesis and in vitro activities of new anticancer duplex drugs linking 2′-deoxy-5-fluorouridine (5-FdU) with 3′-C-ethynylcytidine (ECyd) via a phosphodiester bonding

  摘要：

  Two isomeric cytostatic duplex drugs 2'-deoxy-5-fluorouridylyl-(3'-> 5')-3'-C-ethynylcytidine [5-FdU(3'-> 5')ECyd] and 2'-deoxy-5-fluorouridylyl-(5'-> 5')-3'-C-ethynylcytidine [5-FdU(5'-> 5')ECyd] were designed and synthesized at gram scale according to the hydrogenphosphonate method in an overall yield of about 40%. The in vitro evaluation of the anticancer effects indicated highly varying sensibilities of the panel of 60 tested tumor cell lines against the duplex drugs. 5-FdU(3'-> 5')ECyd had a 50% growth inhibition (IC50 <= 10 (8) M) in 44/58 cell lines. However, only 25/53 of those cell lines showed corresponding IC50 values when the isomeric 5-FdU(5'-> 5')ECyd was tested. Total growth inhibition was achieved using micromolar concentrations of the duplex drugs. The 5-FdU residue of the duplex drug can cause very different effects like additive, synergistic, antagonistic as well as sequence-depending activities, which drastically changed efficiency as well as specificity of the anticancer activities of the duplex drugs, in comparison to those of the monomeric drugs. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2009.08.033