1-ethyl-5-(3-furan-2-ylallylidene)-2-thioxodihydropyrimidine-4,6-dione | 346643-69-4

• 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-ethyl-5-(3-furan-2-ylallylidene)-2-thioxodihydropyrimidine-4,6-dione
• 英文别名: 1-Ethyl-5-[3-(furan-2-yl)prop-2-enylidene]-2-sulfanylidene-1,3-diazinane-4,6-dione
• CAS: 346643-69-4
• 化学式: C₁₃H₁₂N₂O₃S
• mdl: MFCD01828096
• 分子量: 276.316
• InChiKey: HVNYBVYQEWRZQQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  94.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  2-呋喃丙烯醛 、 N-ethyl-2-thiobarbituric acid 在 吡啶 作用下， 以 乙醇 为溶剂， 反应 12.0h， 以85%的产率得到1-ethyl-5-(3-furan-2-ylallylidene)-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

文献信息

• THERAPEUTIC COMPOUNDS FOR BLOCKING DNA SYNTHESIS OF POX VIRUSES
  申请人：RICCIARDI Robert P.

  公开号：US20100035887A1

  公开（公告）日：2010-02-11

  This invention provides methods of inhibiting replication of a poxvirus by contacting a poxvirus with a compound having formula I, formula XXI, formula XXXII, or formula XLI which in turn reduce, inhibit, or abrogate poxvirus DNA polymerase activity and/or its interaction with its processivity factor. Formula I, formula XXI, formula XXXII, or formula XLI can be utilized to treat humans and animals suffering from a poxvirus infection. Pharmaceutical compositions for treating poxvirus infected subjects are also provided.

  本发明提供了一种通过将痘病毒与具有公式I、公式XXI、公式XXXII或公式XLI的化合物接触来抑制痘病毒复制的方法，进而减少、抑制或消除痘病毒DNA聚合酶活性和/或其与其过程性因子的相互作用。公式I、公式XXI、公式XXXII或公式XLI可用于治疗患有痘病毒感染的人类和动物。还提供了用于治疗痘病毒感染受试者的药物组合物。
• US8278342B2
  申请人：——

  公开号：US8278342B2

  公开（公告）日：2012-10-02
• US8524719B2
  申请人：——

  公开号：US8524719B2

  公开（公告）日：2013-09-03
• US9211296B2
  申请人：——

  公开号：US9211296B2

  公开（公告）日：2015-12-15
• Design and synthesis of novel thiobarbituric acid derivatives targeting both wild-type and BRAF-mutated melanoma cells
  作者：Srinivasa Rao Ramisetti、Manoj K. Pandey、Sang Y. Lee、Deepkamal Karelia、Satya Narayan、Shantu Amin、Arun K. Sharma

  DOI：10.1016/j.ejmech.2017.11.006

  日期：2018.1

  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.