1-[2-(phenoxy)ethyl]uracil

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 1-[2-(phenoxy)ethyl]uracil
• 英文别名: 1-(2-phenoxyethyl)pyrimidine-2,4(1H,3H)-dione；1-(2-phenoxyethyl)pyrimidine-2,4-dione
• 化学式: C₁₂H₁₂N₂O₃
• 分子量: 232.239
• InChiKey: FUQWEIFHTSHBFY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  58.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  氯化苄 、 1-[2-(phenoxy)ethyl]uracil 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 25.0h， 以89%的产率得到3-Benzyl-1-(2-phenoxyethyl)pyrimidine-2,4-dione
  参考文献：
  名称：

  N1,N3-disubstituted uracils as nonnucleoside inhibitors of HIV-1 reverse transcriptase

  摘要：

  A series of phenyloxyethyl and cinnamyl derivatives of substituted uracils were synthesized and found to exhibit potent activity against HIV-RT and HIV replication in cell culture. In general, the cinnamyl derivatives proved superior to the phenyloxyethyl derivatives, however 1-[2-(4-methylphenoxy)ethyl]3-(3,5-dimethylbenzyl)uracil (19) exhibited the highest activity (EC50 = 0.27 mu M) thus confirming that the 3-benzyluracil fragment in the NNRTI structure can be regarded as a functional analogue of the benzophenone pharmacophore typically found in NNRTIs. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2012.12.027
• 作为产物：
  描述：

  2-苯氧乙基溴 、 2,4-二(三甲硅氧基)嘧啶 反应 3.0h， 以2.8 g的产率得到1-[2-(phenoxy)ethyl]uracil
  参考文献：
  名称：

  The Silyl Method for the Synthesis of 1[-2(Phenoxy)ethyl]uracils

  摘要：

  DOI：

  10.1007/s10593-005-0246-9

文献信息

• Synthesis of acyclic analogs of pyrimidine nucleosides with aromatic units in the side chain
  作者：M. S. Novikov、A. A. Ozerov、A. K. Brel'、G. N. Solodunova、T. P. Ozerova

  DOI：10.1007/bf01169253

  日期：1996.3
• [EN] CATECHOL DIETHERS AS POTENT ANTI-HIV AGENTS<br/>[FR] DIÉTHERS DE CATÉCHOL COMME AGENTS ANTI-HIV PUISSANTS
  申请人：UNIV YALE

  公开号：WO2013056003A2

  公开（公告）日：2013-04-18

  The present invention is directed to novel catechol diether compounds, pharmaceutical compositions therefrom and methods for inhibiting reverse transcriptase and treating HIV infections, especially included drug resistant strains of HIV 1 and 2 and/or secondary disease states and/or conditions which occur as a consequence of HIV infection.
• N1,N3-disubstituted uracils as nonnucleoside inhibitors of HIV-1 reverse transcriptase
  作者：Mikhail S. Novikov、Vladimir T. Valuev-Elliston、Denis A. Babkov、Maria P. Paramonova、Alexander V. Ivanov、Sergey A Gavryushov、Anastasia L. Khandazhinskaya、Sergey N. Kochetkov、Christophe Pannecouque、Graciela Andrei、Robert Snoeck、Jan Balzarini、Katherine L. Seley-Radtke

  DOI：10.1016/j.bmc.2012.12.027

  日期：2013.3

  A series of phenyloxyethyl and cinnamyl derivatives of substituted uracils were synthesized and found to exhibit potent activity against HIV-RT and HIV replication in cell culture. In general, the cinnamyl derivatives proved superior to the phenyloxyethyl derivatives, however 1-[2-(4-methylphenoxy)ethyl]3-(3,5-dimethylbenzyl)uracil (19) exhibited the highest activity (EC50 = 0.27 mu M) thus confirming that the 3-benzyluracil fragment in the NNRTI structure can be regarded as a functional analogue of the benzophenone pharmacophore typically found in NNRTIs. (C) 2012 Elsevier Ltd. All rights reserved.
• The Silyl Method for the Synthesis of 1[-2(Phenoxy)ethyl]uracils
  作者：M. S. Novikov、A. A. Ozerov

  DOI：10.1007/s10593-005-0246-9

  日期：2005.7