2-[2-(4-Fluoro-phenyl)-2-oxo-ethylsulfanyl]-5-isopropyl-6-naphthalen-1-ylmethyl-3H-pyrimidin-4-one

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-[2-(4-Fluoro-phenyl)-2-oxo-ethylsulfanyl]-5-isopropyl-6-naphthalen-1-ylmethyl-3H-pyrimidin-4-one
• 英文别名: 2-[2-(4-fluorophenyl)-2-oxo-ethyl]sulfanyl-5-isopropyl-4-(1-naphthylmethyl)-1H-pyrimidin-6-one；2-[2-(4-fluorophenyl)-2-oxoethyl]sulfanyl-4-(naphthalen-1-ylmethyl)-5-propan-2-yl-1H-pyrimidin-6-one
• 化学式: C₂₆H₂₃FN₂O₂S
• 分子量: 446.545
• InChiKey: XRYZFDPCOQKKSS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.75
• 重原子数：
  32.0
• 可旋转键数：
  7.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  62.82
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为产物：
  描述：

  1-萘乙腈 在 sodium ethanolate 、 potassium carbonate 、 锌 作用下， 以 四氢呋喃 、 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 6.0h， 生成 2-[2-(4-Fluoro-phenyl)-2-oxo-ethylsulfanyl]-5-isopropyl-6-naphthalen-1-ylmethyl-3H-pyrimidin-4-one
  参考文献：
  名称：

  5-Alkyl-2-[(aryl and alkyloxylcarbonylmethyl)thio]-6-(1-naphthylmethyl) pyrimidin-4(3H)-ones as an unique HIV reverse transcriptase inhibitors of S-DABO series

  摘要：

  The introduction of a beta-carbonyl group to the C-2 side chain of S-DABO led to the finding of a series of novel potent anti-HIV agent. Some derivatives proved to be highly effective in inhibiting HIV-1 replication at nanomolar concentrations. Furthermore, the novel S-DABOs differ from the classical NNRTIs in that some compounds are active against both HIV-1 and HIV-2. They might interfere with another target or at least act on RT in a different way as compared to typical NNRTIs. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.04.008

文献信息

• Nonnucleoside HIV-1 reverse transcriptase inhibitors; part 3. Synthesis and antiviral activity of 5-alkyl-2-[(aryl and alkyloxyl-carbonylmethyl)thio]-6-(1-naphthylmethyl) pyrimidin-4(3H)-ones
  作者：Yanping He、Fener Chen、Xiongjie Yu、Yueping Wang、Erik De Clercq、Jan Balzarini、Christophe Pannecouque

  DOI：10.1016/j.bioorg.2004.05.007

  日期：2004.12

  beta-carbonyl group on the C-2 side chain were synthesized. All of the new compounds were evaluated for their anti-HIV activities in MT-4 cells. The most active compound, 5-isopropyl-2-[(4'-methoxyphenylcarbonyl-methyl)thio]-6-(1-naphthylmethyl)pyrimid in-4(3H)-one showed activity against HIV-1 and against the double mutated strain of HIV(Y181C and K103N) in the micromolar range. Furthermore, some

  合成了一系列在C-2侧链上具有β-羰基的6-萘甲基甲基取代的S-烷基化的二氢烷氧基苄基氧嘧啶（S-DABO）类似物。对所有这些新化合物在MT-4细胞中的抗HIV活性进行了评估。最活泼的化合物4-（3H）-中的5-异丙基-2-[（（4'-甲氧基苯基羰基-甲基）硫基] -6-（1-萘基甲基）嘧啶显示出对HIV-1和双突变的活性。 HIV的菌株（Y181C和K103N）在微摩尔范围内。此外，某些化合物在细胞培养中对HIV-1和HIV-2均具有活性。鉴于这些化合物针对S0561945进行测试时其抗病毒活性的损失远不如典型NNRTI的活性下降那么明显，
• 5-Alkyl-2-[(aryl and alkyloxylcarbonylmethyl)thio]-6-(1-naphthylmethyl) pyrimidin-4(3H)-ones as an unique HIV reverse transcriptase inhibitors of S-DABO series
  作者：Yanping He、Fener Chen、Guangfu Sun、Yueping Wang、Erik De Clercq、Jan Balzarini、Christophe Pannecouque

  DOI：10.1016/j.bmcl.2004.04.008

  日期：2004.6

  The introduction of a beta-carbonyl group to the C-2 side chain of S-DABO led to the finding of a series of novel potent anti-HIV agent. Some derivatives proved to be highly effective in inhibiting HIV-1 replication at nanomolar concentrations. Furthermore, the novel S-DABOs differ from the classical NNRTIs in that some compounds are active against both HIV-1 and HIV-2. They might interfere with another target or at least act on RT in a different way as compared to typical NNRTIs. (C) 2004 Elsevier Ltd. All rights reserved.