trans-6-<2-<(2-hydroxyethyl)thio>vinyl>uracil | 82771-71-9

• 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: trans-6-<2-<(2-hydroxyethyl)thio>vinyl>uracil
• 英文别名: 6-[(E)-2-(2-hydroxyethylsulfanyl)ethenyl]-1H-pyrimidine-2,4-dione
• CAS: 82771-71-9
• 化学式: C₈H₁₀N₂O₃S
• 分子量: 214.245
• InChiKey: YXRLZIXALJICJA-HNQUOIGGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.24
• 重原子数：
  14.0
• 可旋转键数：
  4.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  85.95
• 氢给体数：
  3.0
• 氢受体数：
  4.0

反应信息

• 作为产物：
  描述：

  6-<(trimethylsilyl)ethynyl>uracil 在 甲醇 作用下， 以 水 为溶剂， 反应 33.0h， 生成 trans-6-<2-<(2-hydroxyethyl)thio>vinyl>uracil
  参考文献：
  名称：

  Synthesis and biological evaluation of 6-ethynyluracil, a thiol-specific alkylating pyrimidine

  摘要：

  6-Ethynyluracil (3) was prepared by two different synthetic procedures. In one approach, 6-formyluracil was reacted with (dibromomethylene)triphenylphosphorane to give 6-(2,2-dibromovinyl)uracil (2), which was silylated and treated with phenyllithium to yield 3. Alternatively, silylated 6-iodouracil was reacted with trimethylsilylacetylene in dry triethylamine in the presence of a palladium/copper catalyst to give 6-[(trimethylsilyl)ethynyl]uracil (5). Compound 5 was converted to 3 in refluxing methanol. At neutral pH, 3 reacted with thiols, such as glutathione, 2-mercaptoethanol, and L-cysteine, but did not react with glycine or L-lysine. This reaction was accompanied by a shift in the UV maximum of 3 from 286 nm to 321-325 nm. The reaction of 3 with 2-mercaptoethanol gave cis-6-[2[(2-hydroxyethyl)-thio]vinyl]uracil as the predominant product. Compounds 2 and 3 inhibited the growth of leukemia L1210, B-16 melanoma, and lewis lung carcinoma cells at concentrations ranging from 1 x 10(-6) to 2 x 10(-5) M. As determined with L1210 cells, the inhibition of growth caused by 2 and 3 was not prevented by the natural pyrimidines, indicating that the agents do not act as antimetabolites.

  DOI：

  10.1021/jm00352a034