5-Chloro-1,3-bis(prop-2-ynyl)pyrimidine-2,4-dione | 1416472-63-3

• 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: 5-Chloro-1,3-bis(prop-2-ynyl)pyrimidine-2,4-dione
• 英文别名: 5-chloro-1,3-bis(prop-2-ynyl)pyrimidine-2,4-dione
• CAS: 1416472-63-3
• 化学式: C₁₀H₇ClN₂O₂
• 分子量: 222.631
• InChiKey: GTEHGPQPFMYYSC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  40.6
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-(2-azidoethyl)indoline-2,3-dione 、 5-Chloro-1,3-bis(prop-2-ynyl)pyrimidine-2,4-dione 在 copper(II) sulfate 、 sodium ascorbate 作用下， 以 乙醇 、 水 为溶剂， 反应 8.0h， 以81%的产率得到1-[2-[4-[[5-Chloro-3-[[1-[2-(2,3-dioxoindol-1-yl)ethyl]triazol-4-yl]methyl]-2,4-dioxopyrimidin-1-yl]methyl]triazol-1-yl]ethyl]indole-2,3-dione
  参考文献：
  名称：

  Synthesis of novel 1H-1,2,3-triazole tethered C-5 substituted uracil–isatin conjugates and their cytotoxic evaluation

  摘要：

  The present manuscript describes the synthesis of uracil isatin hybrids via azide-alkyne cycloadditions and their cytotoxic evaluation against three human cancer cell lines viz. HeLa (cervix), MCF-7 (breast) and DU145 (prostate) using MIT assay. The evaluation studies revealed the dependence of cytotoxicity on C-5 substituents of both uracil and isatin as well as the alkyl chain length with compounds 6g and 6k showing IC50 values 18.21 and 13.90 mu M respectively against DU145 cell lines. Most of the synthesized conjugates exhibited considerable selectivity against MCF-7 and DU145 cell lines. (C) 2012 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2012.10.008
• 作为产物：
  描述：

  5-氯尿嘧啶 、 3-溴丙炔 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 6.25h， 生成 5-Chloro-1,3-bis(prop-2-ynyl)pyrimidine-2,4-dione
  参考文献：
  名称：

  Synthesis of novel 1H-1,2,3-triazole tethered C-5 substituted uracil–isatin conjugates and their cytotoxic evaluation

  摘要：

  The present manuscript describes the synthesis of uracil isatin hybrids via azide-alkyne cycloadditions and their cytotoxic evaluation against three human cancer cell lines viz. HeLa (cervix), MCF-7 (breast) and DU145 (prostate) using MIT assay. The evaluation studies revealed the dependence of cytotoxicity on C-5 substituents of both uracil and isatin as well as the alkyl chain length with compounds 6g and 6k showing IC50 values 18.21 and 13.90 mu M respectively against DU145 cell lines. Most of the synthesized conjugates exhibited considerable selectivity against MCF-7 and DU145 cell lines. (C) 2012 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2012.10.008

文献信息

• Synthesis and biological evaluations of mono‐ and bis‐ferrocene uracil derivatives
  作者：Senka Djaković、Ljubica Glavaš‐Obrovac、Jasmina Lapić、Silvija Maračić、Juraj Kirchofer、Marija Knežević、Marijana Jukić、Silvana Raić‐Malić

  DOI：10.1002/aoc.6052

  日期：2021.1

  uracil derivatives showed pronounced and selective cytostatic activities on colon adenocarcinoma (CaCo‐2) and Burkitt lymphoma (Raji) cells, with higher potency and selectivity than the reference drug 5‐fluorouracil. Generation of reactive oxygen species (ROS) in CaCo‐2 and Raji cells when treated with compounds 5b, 5e, and 6d was observed. Bis‐ferrocenyl 5‐chlorouracil 6c induced significant disruption

  合成了由（1,2a，3-三唑）桥联的单（3a - 3e和4a - 4e）和双二茂铁（5a - 5e和6a - 6e）共轭5取代的尿嘧啶衍生物。观察到二茂铁单元和二茂铁与三唑之间的间隔基对自由基清除能力的影响。双二茂铁基尿嘧啶衍生物比其单二茂铁基类似物具有更好的抗增殖活性。双二茂铁基甲基（5b）和卤素取代的（5e，6c和6d）尿嘧啶衍生物对结肠腺癌（CaCo-2）和Burkitt淋巴瘤（Raji）细胞具有明显的选择性细胞抑制活性，其效力和选择性均高于参考药物5-氟尿嘧啶。当用化合物5b，5e和6d处理时，在CaCo-2和Raji细胞中产生了活性氧（ROS）。双二茂铁基5-氯尿嘧啶6c引起线粒体膜电位的显着破坏，并伴随CaCo-2，Raji和急性淋巴细胞白血病（CCRF-CEM）细胞凋亡的激活，而6d引起线粒体功能障碍和CaCo-中的细胞凋亡诱导。 2和Raji细胞。6c的强抗增殖活性6d和6
• Synthesis of novel 1H-1,2,3-triazole tethered C-5 substituted uracil–isatin conjugates and their cytotoxic evaluation
  作者：Kewal Kumar、Sunil Sagar、Luke Esau、Mandeep Kaur、Vipan Kumar

  DOI：10.1016/j.ejmech.2012.10.008

  日期：2012.12

  The present manuscript describes the synthesis of uracil isatin hybrids via azide-alkyne cycloadditions and their cytotoxic evaluation against three human cancer cell lines viz. HeLa (cervix), MCF-7 (breast) and DU145 (prostate) using MIT assay. The evaluation studies revealed the dependence of cytotoxicity on C-5 substituents of both uracil and isatin as well as the alkyl chain length with compounds 6g and 6k showing IC50 values 18.21 and 13.90 mu M respectively against DU145 cell lines. Most of the synthesized conjugates exhibited considerable selectivity against MCF-7 and DU145 cell lines. (C) 2012 Elsevier Masson SAS. All rights reserved.