6-(heptadec-8-enyl)-2-(methylthio)pyrimidin-4(3H)-one | 1464161-34-9

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 6-(heptadec-8-enyl)-2-(methylthio)pyrimidin-4(3H)-one
• 英文别名: 4-heptadec-8-enyl-2-methylsulfanyl-1H-pyrimidin-6-one
• CAS: 1464161-34-9
• 化学式: C₂₂H₃₈N₂OS
• 分子量: 378.623
• InChiKey: WONSSOJSORXBDA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8
• 重原子数：
  26
• 可旋转键数：
  16
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  66.8
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  6-(heptadec-8-enyl)-2-(methylthio)pyrimidin-4(3H)-one 、 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68%的产率得到6-(heptadec-8-enyl)-2-(methylthio)-1-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)pyrimidin-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
• 作为产物：
  描述：

  6-(heptadec-8-enyl)-2-thiouracil 、 碘甲烷 在 potassium hydroxide 作用下， 以 乙醇 为溶剂， 反应 0.5h， 以70%的产率得到6-(heptadec-8-enyl)-2-(methylthio)pyrimidin-4(3H)-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