2-(tert-butyl)-N-(4-fluorobenzyl)-5-hydroxy-6-oxo-1-(3-(phenylsulfonamido)propyl)-1,6-dihydropyrimidine-4-carboxamide

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-(tert-butyl)-N-(4-fluorobenzyl)-5-hydroxy-6-oxo-1-(3-(phenylsulfonamido)propyl)-1,6-dihydropyrimidine-4-carboxamide
• 英文别名: 1-[3-(benzenesulfonamido)propyl]-2-tert-butyl-N-[(4-fluorophenyl)methyl]-5-hydroxy-6-oxo-pyrimidine-4-carboxamide；1-[3-(benzenesulfonamido)propyl]-2-tert-butyl-N-[(4-fluorophenyl)methyl]-5-hydroxy-6-oxopyrimidine-4-carboxamide
• 化学式: C₂₅H₂₉FN₄O₅S
• 分子量: 516.593
• InChiKey: QFIGTHRXTXXYIX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  36
• 可旋转键数：
  10
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  137
• 氢给体数：
  3
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  2-(tert-butyl)-N-(4-fluorobenzyl)-5-hydroxy-6-oxo-1-(3-(phenylsulfonamido)propyl)-1,6-dihydropyrimidine-4-carboxamide 在 sodium hydroxide 作用下， 反应 0.5h， 以85%的产率得到Sodium;1-[3-(benzenesulfonamido)propyl]-2-tert-butyl-4-[(4-fluorophenyl)methylcarbamoyl]-6-oxopyrimidin-5-olate
  参考文献：
  名称：

  Design and synthesis of novel pyrimidone analogues as HIV-1 integrase inhibitors

  摘要：

  A series of novel pyrimidone analogues have been designed and synthesized as HIV-1 integrase (IN) inhibitors. This study demonstrated that introducing a substituent in the N1-position of the pyrimidone scaffold does not significantly influence IN inhibitory activity. Molecular docking studies showed these compounds could occupy the IN active site and form pi-pi interactions with viral DNA nucleotides DC16 and DA17 to displace reactive viral DNA 3'OH and block intasome activity. (c) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.09.018
• 作为产物：
  描述：

  三甲基乙腈 在 吡啶 、 盐酸 、 盐酸羟胺 、 氢气 、 potassium carbonate 、 caesium carbonate 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 水 、 乙酸乙酯 为溶剂， 反应 102.0h， 生成 2-(tert-butyl)-N-(4-fluorobenzyl)-5-hydroxy-6-oxo-1-(3-(phenylsulfonamido)propyl)-1,6-dihydropyrimidine-4-carboxamide
  参考文献：
  名称：

  Design and synthesis of novel pyrimidone analogues as HIV-1 integrase inhibitors

  摘要：

  A series of novel pyrimidone analogues have been designed and synthesized as HIV-1 integrase (IN) inhibitors. This study demonstrated that introducing a substituent in the N1-position of the pyrimidone scaffold does not significantly influence IN inhibitory activity. Molecular docking studies showed these compounds could occupy the IN active site and form pi-pi interactions with viral DNA nucleotides DC16 and DA17 to displace reactive viral DNA 3'OH and block intasome activity. (c) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.09.018

文献信息

• Design and synthesis of novel pyrimidone analogues as HIV-1 integrase inhibitors
  作者：Shenghui Yu、Tino Wilson Sanchez、Yang Liu、Yanzhen Yin、Nouri Neamati、Guisen Zhao

  DOI：10.1016/j.bmcl.2013.09.018

  日期：2013.11

  A series of novel pyrimidone analogues have been designed and synthesized as HIV-1 integrase (IN) inhibitors. This study demonstrated that introducing a substituent in the N1-position of the pyrimidone scaffold does not significantly influence IN inhibitory activity. Molecular docking studies showed these compounds could occupy the IN active site and form pi-pi interactions with viral DNA nucleotides DC16 and DA17 to displace reactive viral DNA 3'OH and block intasome activity. (c) 2013 Elsevier Ltd. All rights reserved.