5-Amino-1-isobutyl-3-methyl-6-nitro-1H-quinazoline-2,4-dione | 101031-70-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 英文名称: 5-Amino-1-isobutyl-3-methyl-6-nitro-1H-quinazoline-2,4-dione
• CAS: 101031-70-3
• 化学式: C₁₃H₁₆N₄O₄
• 分子量: 292.294
• InChiKey: SIKXGHXQISTRGA-UHFFFAOYSA-N

物化性质

• 沸点：
  481.9±55.0 °C(Predicted)
• 密度：
  1.350±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.85
• 重原子数：
  21.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  113.16
• 氢给体数：
  1.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  5-Amino-1-isobutyl-3-methyl-6-nitro-1H-quinazoline-2,4-dione 在 palladium on activated charcoal 盐酸 、 氢气 作用下， 以 乙醇 为溶剂， 反应 19.0h， 生成 6-isobutyl-2-tert-butyl-8-methylimidazo[4,5-f]quinazoline-7,9(6H,8H)-dione
  参考文献：
  名称：

  Inhibition of cyclic nucleotide phosphodiesterases from pig coronary artery by benzo-separated analogs of 3-isobutyl-1-methylxanthine

  摘要：

  The linear and proximal benzo-separated analogues of 7-benzyl-3-isobutyl-1-methylxanthine, 3-isobutyl-1,8-dimethylxanthine, 3-isobutyl-8-tert-butyl-1-methylxanthine, 3-isobutyl-8-(methoxymethyl)-1-methylxanthine , and 1-isoamyl-3-isobutylxanthine have been prepared and assayed as inhibitors of the peak I and peak II forms of cyclic nucleotide phosphodiesterase from pig coronary artery. Most of the benzo analogues were less effective inhibitors of these phosphodiesterases when compared to 3-isobutyl-1-methylxanthine (IBMX) even though the active sites of both enzyme forms tolerated the stretched-out xanthines. Indeed, the linear benzo-separated analogue of 7-benzyl-IBMX was a more potent inhibitor of peak I activity than was IBMX.

  DOI：

  10.1021/jm00156a013
• 作为产物：
  描述：

  3-氯-2-甲基苯胺 在 盐酸 、 potassium permanganate 、 硫酸 、 氨 、 硝酸 、 magnesium sulfate 、 potassium carbonate 、 三乙胺 作用下， 以 甲醇 、 乙醚 、 乙醇 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 57.67h， 生成 5-Amino-1-isobutyl-3-methyl-6-nitro-1H-quinazoline-2,4-dione
  参考文献：
  名称：

  Linear and proximal benzo-separated alkylated xanthines as adenosine-receptor antagonists

  摘要：

  The linear and proximal benzo-separated derivatives of 8-phenyltheophylline, 1,3-diethyl-8-phenylxanthine, 1,3-dipropylxanthine, 1,3-dibutylxanthine, 3-isobutyl-1-methylxanthine, theophylline, caffeine, and isocaffeine have been synthesized and evaluated for affinity at the A1 and A2 adenosine receptors. Although structure-activity relationships in the benzo-separated series differed from the relationships in the simple xanthines, the most potent of the benzo-separated xanthines were about equal in affinity to the most potent of the corresponding xanthines. On the basis of the present results and the diverse structures reported in the literature as non-xanthine adenosine antagonists, it appears that the primary requirement for adenosine-receptor affinity in nonnucleosides is a flat, neutral, fused-ring heterocycle and that once this requirement is met there are numerous potential binding modes.

  DOI：

  10.1021/jm00130a004