5'-deoxy-5-fluoro-N4-(3-methyl-1-butyloxycarbonyl)cytidine-2',3'-carbonate | 1394845-07-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: 5'-deoxy-5-fluoro-N4-(3-methyl-1-butyloxycarbonyl)cytidine-2',3'-carbonate
• 英文别名: 3-methylbutyl N-[1-[(3aR,4R,6R,6aR)-6-methyl-2-oxo-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxol-4-yl]-5-fluoro-2-oxopyrimidin-4-yl]carbamate
• CAS: 1394845-07-8
• 化学式: C₁₆H₂₀FN₃O₇
• 分子量: 385.349
• InChiKey: XVQQIUGPJRZVOE-UORFTKCHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  27
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  116
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  3-甲基丁基氯甲酸酯 在 potassium carbonate 、 sodium hydroxide 作用下， 以 二氯甲烷 、 丙酮 为溶剂， 反应 2.0h， 生成 5'-deoxy-5-fluoro-N4-(3-methyl-1-butyloxycarbonyl)cytidine-2',3'-carbonate
  参考文献：
  名称：

  Synthesis and biological activity evaluation of cytidine-5′-deoxy-5-fluoro-N-[(alkoxy/aryloxy)] carbonyl-cyclic 2′,3′-carbonates

  摘要：

  Capecitabine, an oral prodrug of 5-FU was developed to improve the tumor selectivity and tolerability. To enhance the efficacy of capacitabine, a series of 5'-deoxy-5-fluorocytidine derivatives 5a-e were synthesized. In the present study, we investigated antitumor activity of 5'-deoxy-5-fluorocytidine derivatives both in vivo and in vitro methods. Title compounds were non-mutagenic to Salmonella typhimurium tester strain in Ames test. Compounds 5d and 5e are potent to inhibit the proliferation of NCI-69, PZ-HPV-7, MCF-7 and HeLa cells in MU assay. In particular, 5d and 5e showed potent antitumor activities against L1210 leukemia cell line. Collectively, these findings suggest that 5d and 5e are more potent anti-cancer compounds than capecitabine. Published by Elsevier Masson SAS.

  DOI：

  10.1016/j.ejmech.2012.06.023