4-(4-fluoro-phenyl)-6-methyl-2-tetradecylsulfanyl-1,4-dihydro-pyrimidine-5-carboxylic acid ethyl ester | 1104612-55-6

• 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: 4-(4-fluoro-phenyl)-6-methyl-2-tetradecylsulfanyl-1,4-dihydro-pyrimidine-5-carboxylic acid ethyl ester
• 英文别名: Ethyl 4-(4-fluorophenyl)-6-methyl-2-tetradecylsulfanyl-1,4-dihydropyrimidine-5-carboxylate
• CAS: 1104612-55-6
• 化学式: C₂₈H₄₃FN₂O₂S
• 分子量: 490.726
• InChiKey: XERCXRGBVQOATO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.3
• 重原子数：
  34
• 可旋转键数：
  18
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  76
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  溴代十四烷 、 4-(4-fluoro-phenyl)-6-methyl-2-thioxo-1,2,3,4-tetrahydro-pyrimidine-5-carboxylic acid ethyl ester 在 四丁基溴化铵 、 potassium carbonate 作用下， 以 丙酮 为溶剂， 反应 7.0h， 以85%的产率得到4-(4-fluoro-phenyl)-6-methyl-2-tetradecylsulfanyl-1,4-dihydro-pyrimidine-5-carboxylic acid ethyl ester
  参考文献：
  名称：

  Synthesis of 2-sulfanyl-6-methyl-1,4-dihydropyrimidines as a new class of antifilarial agents

  摘要：

  A series of 2-sulfanyl-6-methyl-1,4-dihydropyrimidines (8-21) were synthesized in good yields by alkylation of 5-methyl-6-phenyl-2-thioxo-1,2,3,6-tetrahydropyrimidine-4-carboxylic acid ethyl esters (2-7) with different alkyl or aralkyl halides in the presence of a combination of anhydrous K2CO3 and catalytic amount of tetrabutyl ammonium bromide. The title compounds were evaluated for their antifilarial activity against adult parasites of human lymphatic filarial parasite Brugia malayi (sub-periodic strain) in vitro and in vivo at various concentrations. One of the compounds (18) showed promising antifilarial activity. (C) 2008 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2008.01.038

文献信息

• Synthesis of 2-sulfanyl-6-methyl-1,4-dihydropyrimidines as a new class of antifilarial agents
  作者：B.K. Singh、Mridul Mishra、Nisha Saxena、G.P. Yadav、P.R. Maulik、M.K. Sahoo、R.L. Gaur、P.K. Murthy、R.P. Tripathi

  DOI：10.1016/j.ejmech.2008.01.038

  日期：2008.12

  A series of 2-sulfanyl-6-methyl-1,4-dihydropyrimidines (8-21) were synthesized in good yields by alkylation of 5-methyl-6-phenyl-2-thioxo-1,2,3,6-tetrahydropyrimidine-4-carboxylic acid ethyl esters (2-7) with different alkyl or aralkyl halides in the presence of a combination of anhydrous K2CO3 and catalytic amount of tetrabutyl ammonium bromide. The title compounds were evaluated for their antifilarial activity against adult parasites of human lymphatic filarial parasite Brugia malayi (sub-periodic strain) in vitro and in vivo at various concentrations. One of the compounds (18) showed promising antifilarial activity. (C) 2008 Elsevier Masson SAS. All rights reserved.