6-乙基-2(1H)-嘧啶硫酮 | 35071-18-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 中文名称: 6-乙基-2(1H)-嘧啶硫酮
• 英文名称: 2-Mercapto-4-ethyl-pyrimidin
• 英文别名: 4-ethyl-2-mercaptopyrimidine；4-ethyl-1H-pyrimidine-2-thione；Ethyl-2-mercaptopyrimidine；6-ethyl-1H-pyrimidine-2-thione
• CAS: 35071-18-2
• 化学式: C₆H₈N₂S
• 分子量: 140.209
• InChiKey: CITFETCXGZIXCA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  9
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  56.5
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  6-乙基-2(1H)-嘧啶硫酮 、 2-(溴二氟甲基)-1,3-苯并噁唑 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 、 mineral oil 为溶剂， 反应 15.17h， 以10%的产率得到2-[difluoro[(4-ethylpyrimidinyl)thio]methyl]benzoxazole
  参考文献：
  名称：

  Difluoromethylbenzoxazole Pyrimidine Thioether Derivatives: A Novel Class of Potent Non-Nucleoside HIV-1 Reverse Transcriptase Inhibitors

  摘要：

  This paper reports the synthesis and antiviral properties of new difluoromethylbenzoxazole (DFMB) pyrimidine thioether derivatives as non-nucleoside HIV-1 reverse transcriptase inhibitors. By use of a combination of structural biology study and traditional medicinal chemistry, several members of this novel class were synthesized using a single electron transfer chain process (radical nucleophilic substitution, Si) and were found to be potent against wild-type HIV-1 reverse transcriptase, with low cytotoxicity but with moderate activity against drug-resistant strains. The most promising compound 2,4 showed a significant EC50 value close to 6.4 nM against HIV-1 IIIB, a moderate EC50 value close to 54 mu M against an NNRTI resistant double mutant (K103N + Y181C), but an excellent selectivity index >15477 (CC50 > 100 mu M).

  DOI：

  10.1021/jm200766b
• 作为产物：
  描述：

  1-(二甲氨基)戊-1-烯-3-酮 、 硫脲 在 sodium methylate 作用下， 以 乙醇 为溶剂， 反应 24.0h， 以10%的产率得到6-乙基-2(1H)-嘧啶硫酮
  参考文献：
  名称：

  Difluoromethylbenzoxazole Pyrimidine Thioether Derivatives: A Novel Class of Potent Non-Nucleoside HIV-1 Reverse Transcriptase Inhibitors

  摘要：

  This paper reports the synthesis and antiviral properties of new difluoromethylbenzoxazole (DFMB) pyrimidine thioether derivatives as non-nucleoside HIV-1 reverse transcriptase inhibitors. By use of a combination of structural biology study and traditional medicinal chemistry, several members of this novel class were synthesized using a single electron transfer chain process (radical nucleophilic substitution, Si) and were found to be potent against wild-type HIV-1 reverse transcriptase, with low cytotoxicity but with moderate activity against drug-resistant strains. The most promising compound 2,4 showed a significant EC50 value close to 6.4 nM against HIV-1 IIIB, a moderate EC50 value close to 54 mu M against an NNRTI resistant double mutant (K103N + Y181C), but an excellent selectivity index >15477 (CC50 > 100 mu M).

  DOI：

  10.1021/jm200766b

文献信息

• Difluoromethylbenzoxazole Pyrimidine Thioether Derivatives: A Novel Class of Potent Non-Nucleoside HIV-1 Reverse Transcriptase Inhibitors
  作者：Jérémie Boyer、Eric Arnoult、Maurice Médebielle、Jérôme Guillemont、Johan Unge、Dirk Jochmans

  DOI：10.1021/jm200766b

  日期：2011.12.8

  This paper reports the synthesis and antiviral properties of new difluoromethylbenzoxazole (DFMB) pyrimidine thioether derivatives as non-nucleoside HIV-1 reverse transcriptase inhibitors. By use of a combination of structural biology study and traditional medicinal chemistry, several members of this novel class were synthesized using a single electron transfer chain process (radical nucleophilic substitution, Si) and were found to be potent against wild-type HIV-1 reverse transcriptase, with low cytotoxicity but with moderate activity against drug-resistant strains. The most promising compound 2,4 showed a significant EC50 value close to 6.4 nM against HIV-1 IIIB, a moderate EC50 value close to 54 mu M against an NNRTI resistant double mutant (K103N + Y181C), but an excellent selectivity index >15477 (CC50 > 100 mu M).