5-fluoro-6-(heptadec-8-enyl)-2-piperazinopyrimidin-4(1H)-one | 1464161-46-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪烷类
• 英文名称: 5-fluoro-6-(heptadec-8-enyl)-2-piperazinopyrimidin-4(1H)-one
• 英文别名: 5-fluoro-4-heptadec-8-enyl-2-piperazin-1-yl-1H-pyrimidin-6-one
• CAS: 1464161-46-3
• 化学式: C₂₅H₄₃FN₄O
• 分子量: 434.641
• InChiKey: LYVZYUPSRWKTAB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.8
• 重原子数：
  31
• 可旋转键数：
  16
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.76
• 拓扑面积：
  56.7
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  6-(heptadec-8-enyl)-2-thiouracil 在 ammonium cerium (IV) nitrate 、 溶剂黄146 、 lithium fluoride 作用下， 以 乙腈 为溶剂， 反应 22.0h， 生成 5-fluoro-6-(heptadec-8-enyl)-2-piperazinopyrimidin-4(1H)-one
  参考文献：
  名称：

  Facile synthesis of 6-(heptadec-8-enyl)thiopyrimidines incorporating glycosyl moiety and their antitumor activity

  摘要：

  A facile, convenient, and high yielding synthesis of a new series of pyrimidine N- and S-glycosides incorporating an oleyl residue from readily available starting materials was developed. The key step of this protocol is the formation of a 2-thioxopyrimidine as aglycon which is coupled with an activated cyclic and acyclic halo sugar in the presence of sodium hydride. In addition, 5-fluorouracil analogues containing an oleyl moiety were prepared. The in vitro anticancer activity of the newly synthesized compounds was evaluated against two human cancer cell lines, namely MCF-7 (breast) and HEPG2 (liver) carcinoma. The compounds exhibited moderate to high activities with IC (50) values of 13.2-34.2 mu M for MCF-7 and 16.2-63.8 mu M for HEPG-2 cell lines. 5-Fluorouracil derivatives incorporating a fatty residue are therefore potent against both cell lines.

  DOI：

  10.1007/s00706-013-1069-5