2-[(5-cyano-6-(4-hydroxyphenyl)-4-phenylaminopyrimidin-2-yl)sulfanyl]-N-[2-(2,4-dichlorophenoxymethyl)-4-oxo-4H-quinazolin-3-yl]acetamide | 1382229-33-5

• 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-(4-hydroxyphenyl)-4-phenylaminopyrimidin-2-yl)sulfanyl]-N-[2-(2,4-dichlorophenoxymethyl)-4-oxo-4H-quinazolin-3-yl]acetamide
• 英文别名: 2-[4-anilino-5-cyano-6-(4-hydroxyphenyl)pyrimidin-2-yl]sulfanyl-N-[2-[(2,4-dichlorophenoxy)methyl]-4-oxoquinazolin-3-yl]acetamide
• CAS: 1382229-33-5
• 化学式: C₃₄H₂₃Cl₂N₇O₄S
• 分子量: 696.573
• InChiKey: CRTWIWYTGRXBRV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.6
• 重原子数：
  48
• 可旋转键数：
  9
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  178
• 氢给体数：
  3
• 氢受体数：
  10

反应信息

• 作为产物：
  描述：

  2-[2-(2,4-dichlorophenoxy)acetylamino]benzoic acid methyl ester 在 potassium carbonate 、 一水合肼 、 三乙胺 、 三氯氧磷 作用下， 以 乙醇 、 丙酮 、 正丁醇 、 苯 为溶剂， 反应 55.5h， 生成 2-[(5-cyano-6-(4-hydroxyphenyl)-4-phenylaminopyrimidin-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

文献信息

• New quinazolinone–pyrimidine hybrids: Synthesis, anti-inflammatory, and ulcerogenicity studies
  作者：Safinaz E. Abbas、Fadi M. Awadallah、Nashwa A. Ibrahin、Eman G. Said、Gihan M. Kamel

  DOI：10.1016/j.ejmech.2012.03.050

  日期：2012.7

  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.