2-(4-acetylbenzylthio)-6-benzyl-5-ethylpyrimidin-4(3H)-one | 1237521-90-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-(4-acetylbenzylthio)-6-benzyl-5-ethylpyrimidin-4(3H)-one
• CAS: 1237521-90-2
• 化学式: C₂₂H₂₂N₂O₂S
• 分子量: 378.495
• InChiKey: WVFCHTVOIZNYDK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.42
• 重原子数：
  27.0
• 可旋转键数：
  7.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  62.82
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  2-(4-acetylbenzylthio)-6-benzyl-5-ethylpyrimidin-4(3H)-one 、 草酸二乙酯 在 乙醇 、 sodium 作用下， 反应 2.0h， 生成 C₂₆H₂₆N₂O₅S
  参考文献：
  名称：

  Pharmacophore and structure–activity relationships of integrase inhibition within a dual inhibitor scaffold of HIV reverse transcriptase and integrase

  摘要：

  Rational design of dually active inhibitors against human immunodeficiency virus (HIV) reverse transcriptase (RT) and integrase (IN) has proved viable with 1-[(2-hydroxyethoxy) methyl]-6-(phenylthio) thymine (HEPT) type of non-nucleoside RT inhibitors (NNRTIs). To establish the pharmacophore and study the structure-activity relationships (SAR) of integrase inhibition within a previously disclosed RT/IN dual inhibitor scaffold, new analogues featuring substitution at different sites of the HEPT ring were designed and synthesized. These studies have revealed an IN inhibition pharmacophore that is merged with the known RT pharmacophore through a shared C-6 benzyl group. Further SAR also demonstrated that optimal IN inhibition within our dual inhibitor scaffold requires a regiospecific (N-1) diketoacid (DKA)-carrying pendant with a certain length. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.05.004
• 作为产物：
  描述：

  1-(4-(溴甲基)苯基)乙酮 、 6-benzyl-5-ethyl-2-thiouracil 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 6.0h， 以50%的产率得到2-(4-acetylbenzylthio)-6-benzyl-5-ethylpyrimidin-4(3H)-one
  参考文献：
  名称：

  Pharmacophore and structure–activity relationships of integrase inhibition within a dual inhibitor scaffold of HIV reverse transcriptase and integrase

  摘要：

  Rational design of dually active inhibitors against human immunodeficiency virus (HIV) reverse transcriptase (RT) and integrase (IN) has proved viable with 1-[(2-hydroxyethoxy) methyl]-6-(phenylthio) thymine (HEPT) type of non-nucleoside RT inhibitors (NNRTIs). To establish the pharmacophore and study the structure-activity relationships (SAR) of integrase inhibition within a previously disclosed RT/IN dual inhibitor scaffold, new analogues featuring substitution at different sites of the HEPT ring were designed and synthesized. These studies have revealed an IN inhibition pharmacophore that is merged with the known RT pharmacophore through a shared C-6 benzyl group. Further SAR also demonstrated that optimal IN inhibition within our dual inhibitor scaffold requires a regiospecific (N-1) diketoacid (DKA)-carrying pendant with a certain length. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.05.004