2-{3-[(6-amino-4-oxo-1,4-dihydropyrimidin-2-yl)sulfanyl]propyl}isoindoline-1,3-dione

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异吲哚及其衍生物
• 英文名称: 2-{3-[(6-amino-4-oxo-1,4-dihydropyrimidin-2-yl)sulfanyl]propyl}isoindoline-1,3-dione
• 英文别名: 2-{3-[(6-Amino-4-oxo-1,4-dihydropyrimidin-2-yl)sulfanyl]-propyl}isoindoline-1,3-dione；2-[3-[(4-amino-6-oxo-1H-pyrimidin-2-yl)sulfanyl]propyl]isoindole-1,3-dione
• 化学式: C₁₅H₁₄N₄O₃S
• 分子量: 330.367
• InChiKey: JCLLCOAFIGNGRY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  130
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  6-氨基-2-硫脲嘧啶 、 N-(3-溴丙基)苯二胺 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 72.0h， 以64%的产率得到2-{3-[(6-amino-4-oxo-1,4-dihydropyrimidin-2-yl)sulfanyl]propyl}isoindoline-1,3-dione
  参考文献：
  名称：

  Synthesis of 2-[(ω-phthalimidoalkyl)sulfanyl]- pyrimidin-4(3H)-ones, their cytotoxicity and in vitro activity against HIV-1/2

  摘要：

  The interaction of N-(2-bromoethyl)- and N-(3-bromopropyl)phthalimides with 2-thiouracils substituted at position 6 was studied in alkaline medium, providing S-monoamidoalkylation products and, depending on the substituents, the products of S,O(4)- and S,N(3)-diamidoalkylation. Among the obtained compounds, only 2-[2-(phthalimidoethyl)sulfanyl]-6-(trifluoromethyl)pyrimidin- 4(3H)-one showed in vitro antiHIV-1 and antiHIV-2 activity at micromolar concentration range.

  DOI：

  10.1007/s10593-020-02624-5

文献信息

• Synthesis of 2-[(ω-phthalimidoalkyl)sulfanyl]- pyrimidin-4(3H)-ones, their cytotoxicity and in vitro activity against HIV-1/2
  作者：Ivan A. Novakov、Dmitry S. Sheikin、Viktor V. Chapurkin、Maksim B. Nawrozkij、Alexande S. Babushkin、Yaroslav P. Kuznetsov、Evsey A. Ruchko、Vadim V. Kachala、Anton Yu. Maryshev、Dominique Schols

  DOI：10.1007/s10593-020-02624-5

  日期：2020.1

  The interaction of N-(2-bromoethyl)- and N-(3-bromopropyl)phthalimides with 2-thiouracils substituted at position 6 was studied in alkaline medium, providing S-monoamidoalkylation products and, depending on the substituents, the products of S,O(4)- and S,N(3)-diamidoalkylation. Among the obtained compounds, only 2-[2-(phthalimidoethyl)sulfanyl]-6-(trifluoromethyl)pyrimidin- 4(3H)-one showed in vitro antiHIV-1 and antiHIV-2 activity at micromolar concentration range.