ethyl 6-{[3-cyano-4-(2-furyl)-6-oxo-1,4,5,6-tetrahydropyridin-2-ylthio]methyl}-4-(4-methoxyphenyl)-1-methyl-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate | 1391631-76-7

• 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: ethyl 6-{[3-cyano-4-(2-furyl)-6-oxo-1,4,5,6-tetrahydropyridin-2-ylthio]methyl}-4-(4-methoxyphenyl)-1-methyl-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate
• 英文别名: ethyl 4-[[5-cyano-4-(furan-2-yl)-2-oxo-3,4-dihydro-1H-pyridin-6-yl]sulfanylmethyl]-6-(4-methoxyphenyl)-3-methyl-2-oxo-1,6-dihydropyrimidine-5-carboxylate
• CAS: 1391631-76-7
• 化学式: C₂₆H₂₆N₄O₆S
• 分子量: 522.582
• InChiKey: VMVCKIZRGNDRHY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  37
• 可旋转键数：
  9
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  159
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  糠醛 以 乙醇 为溶剂， 反应 1.0h， 生成 ethyl 6-{[3-cyano-4-(2-furyl)-6-oxo-1,4,5,6-tetrahydropyridin-2-ylthio]methyl}-4-(4-methoxyphenyl)-1-methyl-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate
  参考文献：
  名称：

  Reaction of ethyl 4-aryl-6-bromomethyl-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxylates with N-methylmorpholinium 3-cyano-1,4-dihydro- and 3-cyano-1,4,5,6-tetrahydropyridine-2-thiolates

  摘要：

  Alkylation of N-methylmorpholinium 4-Ar-1-3-cyano-6-oxo-1,4,5,6-tetrahydropyridine-2-thiolates using ethyl 4-Ar-6-bromomethyl-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxylates (10 % KOH, DMF) gives mixtures of diastereomers of ethyl 4-Ar-6-[(4-Ar-1-3-cyano-1,4,5,6-tetrahydropyridin-2-ylthio)methyl]-1-methyl-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxylates in overall 30-58 % yield. Under these conditions the N-methylmorpholinium 4-Ar1-5-(N-Ar-2-carbamoyl)-3-cyano-6-methyl-1,4-dihydropyridine-2-thiolates undergo aromatization of the dihydropyridine ring to give ethyl 4-Ar-6-[4-Ar-1-5-(N-Ar-2-carbamoyl)-3-cyano-6-methylpyridin-2-ylthio)methyl]-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxylates (37-51 %). In the absence of KOH, only the substituted pyridine-2(1 H)-thione is formed as a product of oxidation of the dihydropyridine ring in the starting substrate. Some of the alkylation products obtained possess weak or moderate antibacterial activity towards the specific strains of Escherichia coli and Bacillus subtilis but are inactive towards Candida albicans and Staphylococcus aureus.

  DOI：

  10.1007/s10593-012-1016-0