benzyl 2-(4-(2-(1H-indol-2-yl)ethylcarbamoyl)-5-hydroxy-6-oxo-1,6-dihydropyrimidin-2-yl)propan-2-ylcarbamate | 1415000-13-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: benzyl 2-(4-(2-(1H-indol-2-yl)ethylcarbamoyl)-5-hydroxy-6-oxo-1,6-dihydropyrimidin-2-yl)propan-2-ylcarbamate
• 英文别名: benzyl N-[2-[5-hydroxy-4-[2-(1H-indol-2-yl)ethylcarbamoyl]-6-oxo-1H-pyrimidin-2-yl]propan-2-yl]carbamate
• CAS: 1415000-13-3
• 化学式: C₂₆H₂₇N₅O₅
• 分子量: 489.531
• InChiKey: QNUHHDWGROPTEF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  36
• 可旋转键数：
  9
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  145
• 氢给体数：
  5
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  (1-氰基-1-甲基乙基)氨基甲酸苄酯 在 羟胺 作用下， 以 甲醇 、 乙醇 、 正庚烷 、 水 、 异丙醇 为溶剂， 反应 23.83h， 生成 benzyl 2-(4-(2-(1H-indol-2-yl)ethylcarbamoyl)-5-hydroxy-6-oxo-1,6-dihydropyrimidin-2-yl)propan-2-ylcarbamate
  参考文献：
  名称：

  Structural modifications of 5,6-dihydroxypyrimidines with anti-HIV activity

  摘要：

  A series of 5,6-dihydroxypyrimidine analogs were synthesized and evaluated for their anti-HIV activity in vitro. Among all of the analogs, several compounds exhibited significant anti-HIV activity, especially 1b and 1e, which showed the most potent anti-HIV activity with EC50 values of 0.14 and 0.15 mu M, and TI (therapeutic index) values of >300 and >900, respectively. Further docking studies revealed that the representative compounds 1e and 3a could meet the HIV-1 integrase inhibition minimal requirements of a chelating domain (two metal ions) and an aromatic domain (pi-pi stacking interactions). (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.09.070