4-(6-amino-2,4-dioxo-3-prop-2-ynyl-1,2,3,4-tetrahydropyrimidin-5-ylcarbamoyl)benzenesulfonic acid 4-nitrophenyl ester | 1161743-36-7

• 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: 4-(6-amino-2,4-dioxo-3-prop-2-ynyl-1,2,3,4-tetrahydropyrimidin-5-ylcarbamoyl)benzenesulfonic acid 4-nitrophenyl ester
• 英文别名: (4-nitrophenyl) 4-[(6-amino-2,4-dioxo-3-prop-2-ynyl-1H-pyrimidin-5-yl)carbamoyl]benzenesulfonate
• CAS: 1161743-36-7
• 化学式: C₂₀H₁₅N₅O₈S
• 分子量: 485.434
• InChiKey: LPWSQOTZIOYYFQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  34
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  202
• 氢给体数：
  3
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  4-(6-amino-2,4-dioxo-3-prop-2-ynyl-1,2,3,4-tetrahydropyrimidin-5-ylcarbamoyl)benzenesulfonic acid 4-nitrophenyl ester 在 硫酸氢铵 、 六甲基二硅氮烷 作用下， 反应 16.0h， 以69.9%的产率得到4-(2,6-dioxo-1-prop-2-ynyl-2,3,6,7-tetrahydro-1H-purin-8-yl)benzenesulfonic acid 4-nitrophenyl ester
  参考文献：
  名称：

  1-Alkyl-8-(piperazine-1-sulfonyl)phenylxanthines: Development and Characterization of Adenosine A_2B Receptor Antagonists and a New Radioligand with Subnanomolar Affinity and Subtype Specificity

  摘要：

  A new series of 1-alkyl-8-(piperazine-1-sulfonyl)phenylxanthines was designed, synthesized, and characterized in radioligand binding and functional assays at A(2B) adenosine receptors. A(2B) antagonists with subnanomolar affinity and high selectivity were discovered. The most potent compounds were 1-ethyl-8-(4-(4-(4-trifluoromethylbenzyl)piperazine-1-sulfonyl)phenyl)xanthine (24, PSB-09120, K-i (human A(2B)) = 0. 157 nM) and 8-(4-(4-(4-chlorobenzyl)piperazine-1-sulfonyl)phenyl)-1-propylxanthine (17, PSB-0788, K-i (human A2(B)) = 0.393 nM). Moreover, 8-(4-(4-(4-chlorophenyl)piperazine-1-sulfonyl)phenyl)-1-propylxanthine (35, PSB-603) was developed as an A(2B)-specific antagonist exhibiting a Ki value of 0.553 nM at the human A2B receptor and virtually no affinity for the human and rat A(1) and A(2A) and the human A(3) receptors up to a concentration of 10 mu M. A tritiated form of the compound was prepared as a new radioligand and characterized in kinetic, saturation, and competition studies. It was shown to be a useful pharmacological tool for the selective labeling of human as well as rodent A(2B) receptors (K-D human A(2B) 0.403 nM, mouse A(2B) 0.351 nM).

  DOI：

  10.1021/jm900413e
• 作为产物：
  描述：

  5,6-diamino-3-prop-2-ynyl-1H,3H-pyrimidine-2,4-dione 、 4-[[p-nitrophenoxy]sulfonyl]benzoic acid 在 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 甲醇 为溶剂， 反应 5.0h， 以76.9%的产率得到4-(6-amino-2,4-dioxo-3-prop-2-ynyl-1,2,3,4-tetrahydropyrimidin-5-ylcarbamoyl)benzenesulfonic acid 4-nitrophenyl ester
  参考文献：
  名称：

  1-Alkyl-8-(piperazine-1-sulfonyl)phenylxanthines: Development and Characterization of Adenosine A_2B Receptor Antagonists and a New Radioligand with Subnanomolar Affinity and Subtype Specificity

  摘要：

  A new series of 1-alkyl-8-(piperazine-1-sulfonyl)phenylxanthines was designed, synthesized, and characterized in radioligand binding and functional assays at A(2B) adenosine receptors. A(2B) antagonists with subnanomolar affinity and high selectivity were discovered. The most potent compounds were 1-ethyl-8-(4-(4-(4-trifluoromethylbenzyl)piperazine-1-sulfonyl)phenyl)xanthine (24, PSB-09120, K-i (human A(2B)) = 0. 157 nM) and 8-(4-(4-(4-chlorobenzyl)piperazine-1-sulfonyl)phenyl)-1-propylxanthine (17, PSB-0788, K-i (human A2(B)) = 0.393 nM). Moreover, 8-(4-(4-(4-chlorophenyl)piperazine-1-sulfonyl)phenyl)-1-propylxanthine (35, PSB-603) was developed as an A(2B)-specific antagonist exhibiting a Ki value of 0.553 nM at the human A2B receptor and virtually no affinity for the human and rat A(1) and A(2A) and the human A(3) receptors up to a concentration of 10 mu M. A tritiated form of the compound was prepared as a new radioligand and characterized in kinetic, saturation, and competition studies. It was shown to be a useful pharmacological tool for the selective labeling of human as well as rodent A(2B) receptors (K-D human A(2B) 0.403 nM, mouse A(2B) 0.351 nM).

  DOI：

  10.1021/jm900413e