1-(2,5-dimethylbenzyl)-6-(2,6-dichlorophenylthio)thymine | 1393847-38-5

• 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-(2,5-dimethylbenzyl)-6-(2,6-dichlorophenylthio)thymine
• 英文别名: 6-(2,6-Dichlorophenyl)sulfanyl-1-[(2,5-dimethylphenyl)methyl]-5-methyl-pyrimidine-2,4-dione；6-(2,6-dichlorophenyl)sulfanyl-1-[(2,5-dimethylphenyl)methyl]-5-methylpyrimidine-2,4-dione
• CAS: 1393847-38-5
• 化学式: C₂₀H₁₈Cl₂N₂O₂S
• 分子量: 421.347
• InChiKey: GXLPZPGUGBKZFP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  27
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  74.7
• 氢给体数：
  1
• 氢受体数：
  3

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 、 苄基三乙基氯化铵 、 potassium carbonate 、 三氯氧磷 作用下， 以 甲醇 、 二甲基亚砜 为溶剂， 反应 8.0h， 生成 1-(2,5-dimethylbenzyl)-6-(2,6-dichlorophenylthio)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

文献信息

• Diverse combinatorial design, synthesis and in vitro evaluation of new HEPT analogues as potential non-nucleoside HIV-1 reverse transcription inhibitors
  作者：Raimon Puig-de-la-Bellacasa、Laura Giménez、Sofia Pettersson、Rosalia Pascual、Encarna Gonzalo、José A. Esté、Bonaventura Clotet、José I. Borrell、Jordi Teixidó

  DOI：10.1016/j.ejmech.2012.04.038

  日期：2012.8

  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, 21,2,3,1} 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.