N'-[1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-methyloxolan-2-yl]-5-fluoro-2-oxopyrimidin-4-yl]-N,N-di(propan-2-yl)ethanimidamide | 1226642-76-7

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 5'-脱氧核糖核苷
• 英文名称: N'-[1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-methyloxolan-2-yl]-5-fluoro-2-oxopyrimidin-4-yl]-N,N-di(propan-2-yl)ethanimidamide
• CAS: 1226642-76-7
• 化学式: C₁₇H₂₇FN₄O₄
• 分子量: 370.424
• InChiKey: HJWBXIWMGVJCHL-DSPGLSBSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  26
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  98
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  N,N-diisopropylethanamide dimethyl acetal 、 5’-脱氧-5-氟胞嘧啶核苷 以 甲醇 为溶剂， 反应 10.0h， 以31.7%的产率得到N'-[1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-methyloxolan-2-yl]-5-fluoro-2-oxopyrimidin-4-yl]-N,N-di(propan-2-yl)ethanimidamide
  参考文献：
  名称：

  Design, synthesis and anti-tumoractivity of novel amidine derivatives of doxifluridine

  摘要：

  A series of novel amidine derivatives of doxifluridine were synthesized using acid amide as the starting material, and their antitumor activity was evaluated in A549 cells. Compounds 10 and 11 demonstrated were more potent than 5-Fu, which was used as a positive control. Compound 10, which were found to be the most potent one with IC50 of 3.2 mu mol/L, was 16 times more potent than 5-Fu with IC50 of 52 mu mol/L to the A549 cells. A new route was designed to synthesize 5'-deoxy-5-fluorocytidine. All compounds were characterized by H-1 NMR, MS and X-ray spectras in detail. (C) 2009 K. Li. Published by Elsevier B.V. on behalf of Chinese Chemical Society. All rights reserved.

  DOI：

  10.1016/j.cclet.2009.10.013

文献信息

• Design, synthesis and anti-tumoractivity of novel amidine derivatives of doxifluridine
  作者：Ji Lu Feng、Hai Ling Sun、Dong Ping Geng、Ke Li

  DOI：10.1016/j.cclet.2009.10.013

  日期：2010.2

  A series of novel amidine derivatives of doxifluridine were synthesized using acid amide as the starting material, and their antitumor activity was evaluated in A549 cells. Compounds 10 and 11 demonstrated were more potent than 5-Fu, which was used as a positive control. Compound 10, which were found to be the most potent one with IC50 of 3.2 mu mol/L, was 16 times more potent than 5-Fu with IC50 of 52 mu mol/L to the A549 cells. A new route was designed to synthesize 5'-deoxy-5-fluorocytidine. All compounds were characterized by H-1 NMR, MS and X-ray spectras in detail. (C) 2009 K. Li. Published by Elsevier B.V. on behalf of Chinese Chemical Society. All rights reserved.