6-benzoyl-5-ethyl-1-((4-fluorobenzyloxy)methyl)pyrimidine-2,4(1H,3H)-dione | 1304033-78-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 6-benzoyl-5-ethyl-1-((4-fluorobenzyloxy)methyl)pyrimidine-2,4(1H,3H)-dione
• CAS: 1304033-78-0
• 化学式: C₂₁H₁₉FN₂O₄
• 分子量: 382.391
• InChiKey: SQDLPRGYKPCFJW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.64
• 重原子数：
  28.0
• 可旋转键数：
  7.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  81.16
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  6-benzoyl-5-ethyl-1-((4-fluorobenzyloxy)methyl)pyrimidine-2,4(1H,3H)-dione 在 sodium hydride 、 间氯过氧苯甲酸 作用下， 以 四氢呋喃 为溶剂， 以56%的产率得到6-benzoyl-5-ethyl-1-((4-fluorobenzyloxy)methyl)-3-hydroxypyrimidine-2,4(1H,3H)-dione
  参考文献：
  名称：

  6-Benzoyl-3-hydroxypyrimidine-2,4-diones as dual inhibitors of HIV reverse transcriptase and integrase

  摘要：

  N-3-Hydroxylation of pyrimidine-2,4-diones was recently found to yield inhibitors of both HIV-1 reverse transcriptase (RT) and integrase (IN). An extended series of analogues featuring a benzoyl group at the C-6 position of the pyrimidine ring was synthesized. Through biochemical studies it was found that these new analogues are dually active against both RT and IN in low micromolar range. Antiviral assays confirmed that these new inhibitors are active against HIV-1 in cell culture at nanomolar to low micromolar range, further validating 3-hydroxypyrimidine-2,4-diones as a viable scaffold for antiviral development. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.02.069
• 作为产物：
  描述：

  (5-ethyl-2,6-dimethoxypyrimidin-4-yl)(phenyl)methanone 在 盐酸 、 N,O-双三甲硅基乙酰胺 、 水 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 生成 6-benzoyl-5-ethyl-1-((4-fluorobenzyloxy)methyl)pyrimidine-2,4(1H,3H)-dione
  参考文献：
  名称：

  6-Benzoyl-3-hydroxypyrimidine-2,4-diones as dual inhibitors of HIV reverse transcriptase and integrase

  摘要：

  N-3-Hydroxylation of pyrimidine-2,4-diones was recently found to yield inhibitors of both HIV-1 reverse transcriptase (RT) and integrase (IN). An extended series of analogues featuring a benzoyl group at the C-6 position of the pyrimidine ring was synthesized. Through biochemical studies it was found that these new analogues are dually active against both RT and IN in low micromolar range. Antiviral assays confirmed that these new inhibitors are active against HIV-1 in cell culture at nanomolar to low micromolar range, further validating 3-hydroxypyrimidine-2,4-diones as a viable scaffold for antiviral development. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.02.069