5-fluoro-2-methylsulfanyl-6-oxo-1,6-dihydro-pyrimidine-4-carboxylic acid ethyl ester | 717-48-6

• 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-fluoro-2-methylsulfanyl-6-oxo-1,6-dihydro-pyrimidine-4-carboxylic acid ethyl ester
• 英文别名: ethyl 2-(methylmercapto)-4-hydroxy-5-fluoro-6-pyrimidinecarboxylate
• CAS: 717-48-6
• 化学式: C₈H₉FN₂O₃S
• 分子量: 232.235
• InChiKey: CNARYFBWRKLNHE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.22
• 重原子数：
  15.0
• 可旋转键数：
  3.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  72.31
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  5-fluoro-2-methylsulfanyl-6-oxo-1,6-dihydro-pyrimidine-4-carboxylic acid ethyl ester 在 N-甲基吗啉 、 盐酸 、 2-乙氧基-1-乙氧碳酰基-1,2-二氢喹啉 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 40.0h， 生成 5-fluoroorotyl-L-leucyl-L-leucine tert-butyl ester
  参考文献：
  名称：

  Anticandidal activity of pyrimidine-peptide conjugates

  摘要：

  The ability of conjugates of peptides and 5-fluorocytosine or 5-fluoroorotic acid to enter Candida albicans was investigated. A number of conjugates of 5-fluoroorotic acid and peptides were synthesized using 1-(ethoxy-carbonyl)-2-ethoxy-1,2-dihydroquinoline as the coupling agent. Orotyl-L-leucyl-L-leucine, 5-fluoro-4-(N-succinamoyl-L-alanyl-L-leucine)-2(1H)-pyrimidinone [a 5-fluorocytosine derivative], and 5-fluoroorotyl-L-leucyl-L-leucine all inhibited the uptake of trimethionine into C. albicans WD 18-4. Inhibition by 5-fluoroorotyl-L-leucyl-L-leucine was competitive as judged using double-reciprocal plots. Evaluation of minimum inhibitory concentrations of peptide-5-fluorocytosine conjugates suggest that these conjugates enter C. albicans in the intact form. These results provide the first experimental evidence that peptides can carry pyrimidines into a eukaryote.

  DOI：

  10.1021/jm00182a019
• 作为产物：
  描述：

  S-甲基异硫脲硫酸盐 、 diethyl 2-oxo-3-fluorobutan-1,4-dioate sodium salt 在 sodium ethanolate 作用下， 以 乙醇 为溶剂， 反应 2.0h， 以2.0 g的产率得到5-fluoro-2-methylsulfanyl-6-oxo-1,6-dihydro-pyrimidine-4-carboxylic acid ethyl ester
  参考文献：
  名称：

  Anticandidal activity of pyrimidine-peptide conjugates

  摘要：

  The ability of conjugates of peptides and 5-fluorocytosine or 5-fluoroorotic acid to enter Candida albicans was investigated. A number of conjugates of 5-fluoroorotic acid and peptides were synthesized using 1-(ethoxy-carbonyl)-2-ethoxy-1,2-dihydroquinoline as the coupling agent. Orotyl-L-leucyl-L-leucine, 5-fluoro-4-(N-succinamoyl-L-alanyl-L-leucine)-2(1H)-pyrimidinone [a 5-fluorocytosine derivative], and 5-fluoroorotyl-L-leucyl-L-leucine all inhibited the uptake of trimethionine into C. albicans WD 18-4. Inhibition by 5-fluoroorotyl-L-leucyl-L-leucine was competitive as judged using double-reciprocal plots. Evaluation of minimum inhibitory concentrations of peptide-5-fluorocytosine conjugates suggest that these conjugates enter C. albicans in the intact form. These results provide the first experimental evidence that peptides can carry pyrimidines into a eukaryote.

  DOI：

  10.1021/jm00182a019

文献信息

• US2802005
  申请人：——

  公开号：——

  公开（公告）日：——