1-allyl-3-ethyl-2-thioxo-dihydro-pyrimidine-4,6-dione | 65959-56-0

• 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: 1-allyl-3-ethyl-2-thioxo-dihydro-pyrimidine-4,6-dione
• 英文别名: 1-ethyl-3-prop-2-enyl-2-sulfanylidene-1,3-diazinane-4,6-dione
• CAS: 65959-56-0
• 化学式: C₉H₁₂N₂O₂S
• 分子量: 212.272
• InChiKey: OYWFARNTDAZLCT-UHFFFAOYSA-N

物化性质

• 沸点：
  290.3±33.0 °C(Predicted)
• 密度：
  1.27±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.54
• 重原子数：
  14.0
• 可旋转键数：
  3.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  40.62
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  肉桂醛 、 1-allyl-3-ethyl-2-thioxo-dihydro-pyrimidine-4,6-dione 在 吡啶 作用下， 以 乙醇 为溶剂， 反应 12.0h， 以82%的产率得到1-allyl-3-ethyl-5-(3-phenylallylidene)-2-thioxodihydropyrimidine-4,6-dione
  参考文献：
  名称：

  Design and synthesis of novel thiobarbituric acid derivatives targeting both wild-type and BRAF-mutated melanoma cells

  摘要：

  A series of novel thio-and seleno-barbituric acid derivatives were synthesized by varying the substituents at N1 and N3 (ethyl, methyl, allyl, and phenyl), and C5 tethered with dienyl and trienyl moieties attached to substituents such as phenyl, 2-furanyl, 2-thiophenyl, l-naphthyl, and 3-pyridyl. The cytotoxic potential of these derivatives was evaluated by using MTT assay against melanoma cell lines expressing either wild-type (CHL-1) or mutant (UACC 903) BRAF gene. Among all, 2b and 8b were identified as the most potent compounds. Both 2b and 8b inhibited viability of various melanoma cells and induced cell death as evidenced by Live and Dead assay. Western blot analysis showed that they induce PARP cleavage and inhibit anti-apoptotic Bcl-2, Bcl-xL and Survivin in a dose-dependent manner within 24 h of the treatment. Novel thiobarbituric acid analogs also inhibited viability of various other solid tumor cell lines, such as pancreatic, breast, and colon. Overall, 2b, 2d, and 8b emerged as the most effective compounds and make good leads for the development of future therapeutic agents. (C) 2017 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2017.11.006
• 作为产物：
  描述：

  N-乙基-N'-2-丙烯-1-基-硫脲 、 丙二酸二乙酯 在 sodium ethanolate 作用下， 以 乙醇 为溶剂， 生成 1-allyl-3-ethyl-2-thioxo-dihydro-pyrimidine-4,6-dione
  参考文献：
  名称：

  Design and synthesis of novel thiobarbituric acid derivatives targeting both wild-type and BRAF-mutated melanoma cells

  摘要：

  A series of novel thio-and seleno-barbituric acid derivatives were synthesized by varying the substituents at N1 and N3 (ethyl, methyl, allyl, and phenyl), and C5 tethered with dienyl and trienyl moieties attached to substituents such as phenyl, 2-furanyl, 2-thiophenyl, l-naphthyl, and 3-pyridyl. The cytotoxic potential of these derivatives was evaluated by using MTT assay against melanoma cell lines expressing either wild-type (CHL-1) or mutant (UACC 903) BRAF gene. Among all, 2b and 8b were identified as the most potent compounds. Both 2b and 8b inhibited viability of various melanoma cells and induced cell death as evidenced by Live and Dead assay. Western blot analysis showed that they induce PARP cleavage and inhibit anti-apoptotic Bcl-2, Bcl-xL and Survivin in a dose-dependent manner within 24 h of the treatment. Novel thiobarbituric acid analogs also inhibited viability of various other solid tumor cell lines, such as pancreatic, breast, and colon. Overall, 2b, 2d, and 8b emerged as the most effective compounds and make good leads for the development of future therapeutic agents. (C) 2017 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2017.11.006