N-(3-(dimethylamino)propyl)-2-(4-fluorobenzyl)-5-hydroxy-6-oxo-1,6-dihydropyrimidine-4-carboxamide | 1235863-07-6

• 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: N-(3-(dimethylamino)propyl)-2-(4-fluorobenzyl)-5-hydroxy-6-oxo-1,6-dihydropyrimidine-4-carboxamide
• 英文别名: N-[3-(dimethylamino)propyl]-2-[(4-fluorophenyl)methyl]-5-hydroxy-6-oxo-1H-pyrimidine-4-carboxamide
• CAS: 1235863-07-6
• 化学式: C₁₇H₂₁FN₄O₃
• 分子量: 348.377
• InChiKey: NSXBSSCJRWCXIH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  25
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  94
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  methyl 2-(4-fluorobenzyl)-5-hydroxy-6-oxo-1,6-dihydropyrimidine-4-carboxylate 、 N,N-二甲基-1,3-二氨基丙烷 以 甲醇 为溶剂， 反应 0.17h， 以59%的产率得到N-(3-(dimethylamino)propyl)-2-(4-fluorobenzyl)-5-hydroxy-6-oxo-1,6-dihydropyrimidine-4-carboxamide
  参考文献：
  名称：

  Scaffold rearrangement of dihydroxypyrimidine inhibitors of HIV integrase: Docking model revisited

  摘要：

  A series of dihydroxypyrimidine (DHP) derivatives were designed as inhibitors of HIV integrase (IN) based on known homology models. Through chemical synthesis and biochemical assays it was found that the activity profile of these compounds largely deviates from predictions with existing models. With the recently disclosed IN crystal structure of prototype foamy virus (PFV), a new HIV IN homology model was constructed featuring a critical IN/DNA interface previously lacking. With this new model, docking results completely corroborated observed biological activities. This new model should provide a more accurate and improved platform for the design of new inhibitors of HIV IN. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.04.048

文献信息

• Scaffold rearrangement of dihydroxypyrimidine inhibitors of HIV integrase: Docking model revisited
  作者：Jing Tang、Kasthuraiah Maddali、Yves Pommier、Yuk Y. Sham、Zhengqiang Wang

  DOI：10.1016/j.bmcl.2010.04.048

  日期：2010.6

  A series of dihydroxypyrimidine (DHP) derivatives were designed as inhibitors of HIV integrase (IN) based on known homology models. Through chemical synthesis and biochemical assays it was found that the activity profile of these compounds largely deviates from predictions with existing models. With the recently disclosed IN crystal structure of prototype foamy virus (PFV), a new HIV IN homology model was constructed featuring a critical IN/DNA interface previously lacking. With this new model, docking results completely corroborated observed biological activities. This new model should provide a more accurate and improved platform for the design of new inhibitors of HIV IN. (C) 2010 Elsevier Ltd. All rights reserved.