1-((2-trimethylsilylethoxy)methyl)-6-(3-aminophenylthio)thymine | 1393847-30-7

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 1-((2-trimethylsilylethoxy)methyl)-6-(3-aminophenylthio)thymine
• 英文别名: 6-(3-Aminophenyl)sulfanyl-5-methyl-1-(2-trimethylsilylethoxymethyl)pyrimidine-2,4-dione
• CAS: 1393847-30-7
• 化学式: C₁₇H₂₅N₃O₃SSi
• 分子量: 379.555
• InChiKey: IPUFHNMJYRIYFX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.89
• 重原子数：
  25
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  110
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  5-甲基嘧啶-2,4,6(1H,3H,5H)-三酮 在 sodium tetrahydroborate 、 N,O-双三甲硅基乙酰胺 、 苄基三乙基氯化铵 、 三氯氧磷 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 11.0h， 生成 1-((2-trimethylsilylethoxy)methyl)-6-(3-aminophenylthio)thymine
  参考文献：
  名称：

  Diverse combinatorial design, synthesis and in vitro evaluation of new HEPT analogues as potential non-nucleoside HIV-1 reverse transcription inhibitors

  摘要：

  New analogues of 1-[(2-hydroxyethoxy)methyl]-6-(phenylthio)thymine (HEPT) were synthesized and evaluated for their in vitro activities against HIV-1 in MT-4 cell cultures. Chemical diversity was introduced in 4 of the six positions of the core and the influence of each substituent was studied. This library was built on the basis of a rational diversity analysis with the objective of maximizing diversity and thus, the activity range with a minimum number of synthesized compounds. Among them, 2{1,2,3,1} and 2 {1,2,3,4} exhibited the most potent anti-HIV-1 activities (EC50 = 0.015 mu g/mL; 0.046 mu M, SI > 1667) and (EC50 = 0.025 mu g/mL; 0.086 mu M, SI > 1000), respectively, which were about 71-fold and 38-fold more active than the reference compound HEPT (EC50 = 1.01 mu g/ml; 3.27 mu M, SI > 25). (C) 2012 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2012.04.038