1-(ethoxymethyl)-5-ethyl-6-(4-fluorobenzyl)pyrimidine-2,4(1H,3H)-dione | 1254831-94-1

• 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: 1-(ethoxymethyl)-5-ethyl-6-(4-fluorobenzyl)pyrimidine-2,4(1H,3H)-dione
• CAS: 1254831-94-1
• 化学式: C₁₇H₂₁FN₂O₃
• 分子量: 320.364
• InChiKey: JVRQASPXFHSNAP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.38
• 重原子数：
  23.0
• 可旋转键数：
  6.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  64.09
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  1-(ethoxymethyl)-5-ethyl-6-(4-fluorobenzyl)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， 反应 1.0h， 以63%的产率得到1-(ethoxymethyl)-6-(4-fluorobenzyl)-3-hydroxy-5-isopropylpyrimidine-2,4(1H,3H)-dione
  参考文献：
  名称：

  N-3 Hydroxylation of Pyrimidine-2,4-diones Yields Dual Inhibitors of HIV Reverse Transcriptase and Integrase

  摘要：

  A new molecular scaffold featuring an N-hydroxyimide functionality and capable of inhibiting both reverse transcriptase (RT) and integrase (IN) of human immunodeficiency virus (HIV) was rationally designed based on 1-[(2-hydroxyethoxy)methyl]-6-(phenylthio)thymine (HEPT) non-nucleoside RT inhibitors (NNRTIs). The design involves a minimal 3-N hydroxylation of the pyrimidine ring of HEPT compound to yield a chelating triad which, along with the existing benzyl group, appeared to satisfy major structural requirements for IN binding. In the mean time, this chemical modification did not severely compromise the compound's ability to inhibit RT. A preliminary structure-activity relationship (SAR) study reveals that this N-3 OH is essential for IN inhibition and that the benzyl group on N-1 side chain is more important for IN binding than the one on C-6.

  DOI：

  10.1021/ml1002162
• 作为产物：
  描述：

  对氟苯乙腈 在 N,O-双三甲硅基乙酰胺 、 potassium tert-butylate 、 碘 、 四丁基碘化铵 、 锌 作用下， 以 四氢呋喃 、 二氯甲烷 、 异丙醇 为溶剂， 生成 1-(ethoxymethyl)-5-ethyl-6-(4-fluorobenzyl)pyrimidine-2,4(1H,3H)-dione
  参考文献：
  名称：

  N-3 Hydroxylation of Pyrimidine-2,4-diones Yields Dual Inhibitors of HIV Reverse Transcriptase and Integrase

  摘要：

  A new molecular scaffold featuring an N-hydroxyimide functionality and capable of inhibiting both reverse transcriptase (RT) and integrase (IN) of human immunodeficiency virus (HIV) was rationally designed based on 1-[(2-hydroxyethoxy)methyl]-6-(phenylthio)thymine (HEPT) non-nucleoside RT inhibitors (NNRTIs). The design involves a minimal 3-N hydroxylation of the pyrimidine ring of HEPT compound to yield a chelating triad which, along with the existing benzyl group, appeared to satisfy major structural requirements for IN binding. In the mean time, this chemical modification did not severely compromise the compound's ability to inhibit RT. A preliminary structure-activity relationship (SAR) study reveals that this N-3 OH is essential for IN inhibition and that the benzyl group on N-1 side chain is more important for IN binding than the one on C-6.

  DOI：

  10.1021/ml1002162