6-(heptadec-8-enyl)-2-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosylthio)pyrimidin-4(1H)-one | 1464161-30-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 6-(heptadec-8-enyl)-2-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosylthio)pyrimidin-4(1H)-one
• CAS: 1464161-30-5
• 化学式: C₃₅H₅₄N₂O₁₀S
• 分子量: 694.887
• InChiKey: NGCBZRRDZBTHGF-WJYBGUOCSA-N

反应信息

• 作为产物：
  描述：

  6-(heptadec-8-enyl)-2-thiouracil 、 2,3,4,6-四乙酰氧基-alpha-D-吡喃葡萄糖溴化物 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 1.75h， 以42.857%的产率得到
  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