4-(4-bromophenyl)-6-(2-hydroxyphenyl)-1H-pyrimidine-2-thione | 1352131-29-3

• 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: 4-(4-bromophenyl)-6-(2-hydroxyphenyl)-1H-pyrimidine-2-thione
• CAS: 1352131-29-3
• 化学式: C₁₆H₁₁BrN₂OS
• 分子量: 359.246
• InChiKey: RSEYDOAEQDGRGN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  76.7
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  2'-羟基苯乙酮 在 sodium hydroxide 作用下， 以 乙醇 为溶剂， 反应 12.0h， 生成 4-(4-bromophenyl)-6-(2-hydroxyphenyl)-1H-pyrimidine-2-thione
  参考文献：
  名称：

  Synthesis and biological evaluation of novel pyrimidine-2(1H)-ones/thiones as potent anti-inflammatory and anticancer agents

  摘要：

  Recently there has been an increased interest in the synthesis of pyrimidinone and their applications in medicinal chemistry. Pyrimidinone derivatives represent one of the active classes of the compounds possessing a wide spectrum of biological activities such as anti-tumour, anti-fungal, anti-inflammatory, anti-bacterial, etc. This study utilises chalcones as starting compounds that are obtained by Claisen-Schmidt condensation. These chalcones underwent cyclisation upon treatment with urea and thiourea in the presence of sodium hydroxide to obtain the corresponding pyrimidinones and pyrimidinethiones. The structures of the synthesized compounds were investigated by means of UV, IR, H-1 NMR and Mass spectral analysis. The anti-oxidant activity of the compounds was measured by standard free radical scavenging assays (DPPH, Nitric oxide radicals). The compounds with significant anti-oxidant activity were then screened for the in vivo anti-inflammatory activity and it showed that the compounds ETT and DMT possess good activity as comparable to the standard. All the synthesized compounds were evaluated for their in vitro anti-cancer activity by MTT assay among which compounds CLU and ETU showed significant activity against HeLa and HepG(2) cell lines, respectively.

  DOI：

  10.1007/s00044-011-9909-5

文献信息

• Synthesis and biological evaluation of novel pyrimidine-2(1H)-ones/thiones as potent anti-inflammatory and anticancer agents
  作者：Vachala Seekarajapuram Dinakaran、Divya Jacob、Jessy Elizabeth Mathew

  DOI：10.1007/s00044-011-9909-5

  日期：2012.11

  Recently there has been an increased interest in the synthesis of pyrimidinone and their applications in medicinal chemistry. Pyrimidinone derivatives represent one of the active classes of the compounds possessing a wide spectrum of biological activities such as anti-tumour, anti-fungal, anti-inflammatory, anti-bacterial, etc. This study utilises chalcones as starting compounds that are obtained by Claisen-Schmidt condensation. These chalcones underwent cyclisation upon treatment with urea and thiourea in the presence of sodium hydroxide to obtain the corresponding pyrimidinones and pyrimidinethiones. The structures of the synthesized compounds were investigated by means of UV, IR, H-1 NMR and Mass spectral analysis. The anti-oxidant activity of the compounds was measured by standard free radical scavenging assays (DPPH, Nitric oxide radicals). The compounds with significant anti-oxidant activity were then screened for the in vivo anti-inflammatory activity and it showed that the compounds ETT and DMT possess good activity as comparable to the standard. All the synthesized compounds were evaluated for their in vitro anti-cancer activity by MTT assay among which compounds CLU and ETU showed significant activity against HeLa and HepG(2) cell lines, respectively.