6-(4-chloro-benzyl)-2-thioxo-2,3-dihydro-1H-pyrimidin-4-one | 221121-51-3

• 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: 6-(4-chloro-benzyl)-2-thioxo-2,3-dihydro-1H-pyrimidin-4-one
• 英文别名: 6-(4-Chlor-benzyl)-2-thioxo-2,3-dihydro-1H-pyrimidin-4-on；6-(4-chloro-benzyl)-2-thioxo-2,3-dihydro-1H-pyrimidin-4-one；6-[(4-chlorophenyl)methyl]-2-sulfanylidene-1H-pyrimidin-4-one
• CAS: 221121-51-3
• 化学式: C₁₁H₉ClN₂OS
• 分子量: 252.724
• InChiKey: VMJVXLOVYYOMIO-UHFFFAOYSA-N

物化性质

• 熔点：
  242-243 °C
• 密度：
  1.43±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  73.2
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  6-(4-chloro-benzyl)-2-thioxo-2,3-dihydro-1H-pyrimidin-4-one 在 ammonium hydroxide 作用下， 反应 3.0h， 以86.5%的产率得到6-(4-Chlorobenzyl)pyrimidin-4-ol
  参考文献：
  名称：

  一类含取代基嘧啶芳基脒类化合物、其制备方法及应用

  摘要：

  本发明公开了一种具有通式F-1所示的含取代基嘧啶芳基脒类化合物，各取代基的定义见说明书本发明提供的含取代基嘧啶芳基脒类化合物合成及用于防治真菌病害。

  公开号：

  CN107200712A
• 作为产物：
  描述：

  2-(4-Chloro-phenyl)-1-imidazol-1-yl-ethanone 在 sodium ethanolate 、 三乙胺 、 magnesium chloride 作用下， 以 乙醇 为溶剂， 反应 9.0h， 生成 6-(4-chloro-benzyl)-2-thioxo-2,3-dihydro-1H-pyrimidin-4-one
  参考文献：
  名称：

  5-Alkyl-2-(alkylthio)-6-(2,6-dihalophenylmethyl)-3,4-dihydropyrimidin-4(3H)-ones:  Novel Potent and Selective Dihydro-alkoxy-benzyl-oxopyrimidine Derivatives

  摘要：

  Molecular modeling analysis of compounds belonging to the recently published series of dihydroalkoxy-benzyl-oxopyrimidines (DABOs), such as S-DABOs and DATNOs, gave support to the design of new 2,6-disubstituted benzyl-DABO derivatives as highly potent and specific inhibitors of the HIV-1 reverse transcriptase (RT). To follow up on the novel DABO derivatives, we decided to investigate the effect of electron-withdrawing substituents in the benzyl unit of the S-DABO skeleton versus their anti-HIV-1 activity. Such chemical modifications impacted the inhibitory activity, especially when two halogen units were introduced at positions 2 and 6 in the phenyl portion of the benzyl group bound to C-6 of the pyrimidine ring. Various 5-alkyl-2-(alkyl(or cycloalkyl)thio)-6-(2,B-dichloro(or 2, 6-difluoro)phenylmethyl)-3,4-dihydropyrimidin-4(3H)-ones were then synthesized and tested as anti-HIV-1 agents in both cell-based and enzyme (recombinant reverse transcriptase, rRT) assays. Among the various mono- and disubstituted phenyl derivatives, the most potent were those containing a 6-(2,6-difluorophenylmethyl) substituent (F-DABOs), which showed EC50's ranging between 40 and 90 nM and selectivity indexes up to greater than or equal to 5000. An excellent correlation was found between EC50 and IC50 values which confirmed that these compounds act as inhibitors of the HIV-1 RT. The structure-activity relationships of the newly synthesized pyrimidinones are presented herein.

  DOI：

  10.1021/jm980260f

文献信息

• The Synthesis of Some 6-Substituted-2-thiouracils¹
  作者：Wilbur H. Miller、Alice M. Dessert、George W. Anderson

  DOI：10.1021/ja01182a020

  日期：1948.2