8-amino-2,2-bis<(benzyloxy)methyl>-1H,2H,4H-pyrimido<1,6-c><1,3>oxazine-6-one | 139871-36-6

• 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: 8-amino-2,2-bis<(benzyloxy)methyl>-1H,2H,4H-pyrimido<1,6-c><1,3>oxazine-6-one
• 英文别名: 6-amino-3,3-bis(phenylmethoxymethyl)-1,4-dihydropyrimido[1,6-c][1,3]oxazin-8-one
• CAS: 139871-36-6
• 化学式: C₂₃H₂₅N₃O₄
• 分子量: 407.469
• InChiKey: VHDMTKOMSKXCKW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.53
• 重原子数：
  30.0
• 可旋转键数：
  8.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  88.6
• 氢给体数：
  1.0
• 氢受体数：
  7.0

反应信息

• 作为产物：
  描述：

  1,3-双(苄氧基)-2-丙醇 在 N-氯代丁二酰亚胺 、 正丁基锂 、 二甲基硫 、 氨 、 碘 、 乙酸酐 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 152.42h， 生成 8-amino-2,2-bis<(benzyloxy)methyl>-1H,2H,4H-pyrimido<1,6-c><1,3>oxazine-6-one
  参考文献：
  名称：

  Synthesis of anti-restricted pyrimidine acyclic nucleosides

  摘要：

  A number of pyrimidine acyclic nucleosides which are constrained in the anti conformation have been prepared via treatment of 5,6-dimethyl-2,4-dimethoxypyrimidine or 6-methyl-2,4-dimethoxypyrimidine with 1,3-bis-(benzyloxy)-2-propanone (3) to give 6-[[2-[1,3-bis(benzyloxy)-2-hydroxypropyl]]methyl]-2,4-dimethoxy-5-methylpyrimidine (5a) and 5b, respectively. Using acetic anhydride in DMSO, these compounds were converted to a 2-[[(methylthio)methyl]oxy] intermediate which was annulated to afford 2,2-bis[(benzyloxy)methyl]-8-methoxy-9-methyl-1H,2H,4H-pyrimido[1,6-c][1,3]oxazin-6-one (7a) and 7b, respectively, by using iodine in THF. Nucleophilic replacements at the 8-position and deblocking of 7a and 7b furnished the target compounds, 2,2-bis(hydroxymethyl)-9-methyl-(1H,4H,7H)-pyrimido[1,6-c][1,3]oxazine-6,8-dione (9a) and 9b, and the cytidine derivatives, 8-amino-2,2-bis(hydroxymethyl)-9-methyl-1H,4H-pyrimido[1,6-c][1,3]oxazin-6-one (12a) and 12b. Compounds 8b, 9a, 9b, 10b, 11b, 12a, and 12b were evaluated for activity against herpes viruses and human immunodeficiency virus (HIV). Compound 12a was slightly active against HIV at noncytotoxic concentrations. All other compounds were inactive at the highest concentration tested (100-mu-M).

  DOI：

  10.1021/jo00038a025