2-((5-cyano-6-oxo-4-phenyl-1,6-dihydropyrimidin-2-yl)sulfanyl)-N-[2-(2,4-dichlorophenoxymethyl)-4-oxo-4H-quinazolin-3-yl]acetamide | 1382228-52-5

• 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: 2-((5-cyano-6-oxo-4-phenyl-1,6-dihydropyrimidin-2-yl)sulfanyl)-N-[2-(2,4-dichlorophenoxymethyl)-4-oxo-4H-quinazolin-3-yl]acetamide
• 英文别名: 2-[(5-cyano-6-oxo-4-phenyl-1H-pyrimidin-2-yl)sulfanyl]-N-[2-[(2,4-dichlorophenoxy)methyl]-4-oxoquinazolin-3-yl]acetamide
• CAS: 1382228-52-5
• 化学式: C₂₈H₁₈Cl₂N₆O₄S
• 分子量: 605.461
• InChiKey: TVRHWWUNYMKEGU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  41
• 可旋转键数：
  7
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  162
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  2-((5-cyano-6-oxo-4-phenyl-1,6-dihydropyrimidin-2-yl)sulfanyl)-N-[2-(2,4-dichlorophenoxymethyl)-4-oxo-4H-quinazolin-3-yl]acetamide 在 三乙胺 、 三氯氧磷 作用下， 以 乙醇 为溶剂， 反应 35.5h， 生成 2-[(5-cyano-4-(4-hydroxyphenylamino)-6-phenylpyrimidin-2-yl)sulfanyl]-N-[2-(2,4-dichlorophenoxymethyl)-4-oxo-4H-quinazolin-3-yl]acetamide
  参考文献：
  名称：

  New quinazolinone–pyrimidine hybrids: Synthesis, anti-inflammatory, and ulcerogenicity studies

  摘要：

  Two groups of hybrid compounds: the quinazolinone dihydropyrimidines and quinazolinone pyrimidines, were synthesized. The starting derivative 3 was reacted with chloroacetyl chloride to give intermediate 5 which was condensed with the 2-mercaptopyrimidines 4a-c affording compounds 6a-c. These latter compounds underwent hydrolysis and N-alkylation reactions to give the dihydropyrimidine derivatives 7a-c and 8a-f, respectively. The chloro derivatives 9a-c subsequently reacted with various anilines furnishing compounds 10a-i. The anti-inflammatory activity of the synthesized compounds were evaluated using the carrageenan-induced rat paw oedema model and ulcer indices for the most active compounds were calculated. Five compounds were found more active and less ulcerogenic than diclofenac particularly compound 10g (IC50 = 116.73 mu mol/kg; ulcer index = 11.38). Compound 10g was also 2-fold more selective inhibitor of COX-2 than COX-1. (C) 2012 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2012.03.050
• 作为产物：
  描述：

  2-(2,6-二氯苯氧基)乙酰氯 在 potassium carbonate 、 一水合肼 、 三乙胺 作用下， 以 乙醚 、 丙酮 、 正丁醇 、 苯 为溶剂， 反应 44.0h， 生成 2-((5-cyano-6-oxo-4-phenyl-1,6-dihydropyrimidin-2-yl)sulfanyl)-N-[2-(2,4-dichlorophenoxymethyl)-4-oxo-4H-quinazolin-3-yl]acetamide
  参考文献：
  名称：

  New quinazolinone–pyrimidine hybrids: Synthesis, anti-inflammatory, and ulcerogenicity studies

  摘要：

  Two groups of hybrid compounds: the quinazolinone dihydropyrimidines and quinazolinone pyrimidines, were synthesized. The starting derivative 3 was reacted with chloroacetyl chloride to give intermediate 5 which was condensed with the 2-mercaptopyrimidines 4a-c affording compounds 6a-c. These latter compounds underwent hydrolysis and N-alkylation reactions to give the dihydropyrimidine derivatives 7a-c and 8a-f, respectively. The chloro derivatives 9a-c subsequently reacted with various anilines furnishing compounds 10a-i. The anti-inflammatory activity of the synthesized compounds were evaluated using the carrageenan-induced rat paw oedema model and ulcer indices for the most active compounds were calculated. Five compounds were found more active and less ulcerogenic than diclofenac particularly compound 10g (IC50 = 116.73 mu mol/kg; ulcer index = 11.38). Compound 10g was also 2-fold more selective inhibitor of COX-2 than COX-1. (C) 2012 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2012.03.050