6-(3,5-dimethylbenzyl)-5-methyl-2-(4-nitrobenzylsulfanyl)-pyrimidin-4(3H)-one | 1147724-06-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 6-(3,5-dimethylbenzyl)-5-methyl-2-(4-nitrobenzylsulfanyl)-pyrimidin-4(3H)-one
• 英文别名: 6-(3,5-Dimethylbenzyl)-5-methyl-2-(4-nitrobenzylsulfanyl)-pyrimidin-4(3H)-one；4-[(3,5-dimethylphenyl)methyl]-5-methyl-2-[(4-nitrophenyl)methylsulfanyl]-1H-pyrimidin-6-one
• CAS: 1147724-06-8
• 化学式: C₂₁H₂₁N₃O₃S
• 分子量: 395.482
• InChiKey: XQDMLRWWYVLJAE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  28
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  113
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  6-[(3,5-dimethylphenyl)methyl]-5-methyl-2-sulfanylidene-1H-pyrimidin-4-one 、 alkaline earth salt of/the/ methylsulfuric acid 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 18.0h， 以47.41%的产率得到6-(3,5-dimethylbenzyl)-5-methyl-2-(4-nitrobenzylsulfanyl)-pyrimidin-4(3H)-one
  参考文献：
  名称：

  Synthesis and in vitro anti-HIV evaluation of a new series of 6-arylmethyl-substituted S-DABOs as potential non-nucleoside HIV-1 reverse transcriptase inhibitors

  摘要：

  A series of new 5-alkyl-2-benzylsulfanylpyrimidin-4(3H)-ones (5a-y) bearing different substituted arylmethyl moieties at the C-6 position of the pyrimidine core have been synthesized and evaluated for their in vitro activities against HIV-1 and HIV-2 in MT-4 cell cultures. The majority of the title compounds showed moderate to good activities against HIV-1 with an IC50 range from 6.67 mu M to 0.12 mu M. Among them, 6-(3,5-dimethylbenzy]) analogue 5q exhibited the most potent anti-HIV-1 activity (IC50 = 0.12 mu M, SI > 2642), which was about 40-fold more active than the reference compounds 1-[(2-hydroxyethoxy)methyl]-6-(phenylsulfanyl)thymine (HEPT) and 2',3'-dideoxyinosine (DDI). The structure-activity relationships (SARs) of these new congeners were further discussed. (C) 2008 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2008.06.028