(4-Benzyl-5-propan-2-yl-6-trimethylsilyloxypyrimidin-2-yl)oxy-trimethylsilane | 1020069-04-8

• 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: (4-Benzyl-5-propan-2-yl-6-trimethylsilyloxypyrimidin-2-yl)oxy-trimethylsilane
• CAS: 1020069-04-8
• 化学式: C₂₀H₃₂N₂O₂Si₂
• 分子量: 388.657
• InChiKey: WLUUMHOAOFMNMN-UHFFFAOYSA-N

物化性质

• 沸点：
  422.2±55.0 °C(Predicted)
• 密度：
  0.994±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.62
• 重原子数：
  26
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  44.2
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (4-Benzyl-5-propan-2-yl-6-trimethylsilyloxypyrimidin-2-yl)oxy-trimethylsilane 、 氯甲基乙醚 在 四丁基碘化铵 作用下， 以83%的产率得到1-(乙氧基甲基)-6-(苯基甲基)-5-丙-2-基嘧啶-2,4-二酮
  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：

  N,O-双三甲硅基乙酰胺 、 6-benzyl-5-isopropylpyrimidine-2,4(1H,3H)-dione 以 二氯甲烷 为溶剂， 反应 0.33h， 生成 (4-Benzyl-5-propan-2-yl-6-trimethylsilyloxypyrimidin-2-yl)oxy-trimethylsilane
  参考文献：
  名称：

  Synthesis of pyrimidine and quinolone conjugates as a scaffold for dual inhibitors of HIV reverse transcriptase and integrase

  摘要：

  A series of conjugates combining a pyrimidine and a quinolone moiety were designed and synthesized. The assay results show that these compounds demonstrate both anti-RT activity and anti-IN activity and therefore provide a useful scaffold for identifying inhibitors with balanced dual activities. Published by Elsevier Ltd.

  DOI：

  10.1016/j.bmcl.2008.01.025

文献信息

• Tronchet; Apparu-Turquois; Laroze, Annales Pharmaceutiques Francaises, 2002, vol. 60, # 4, p. 227 - 231
  作者：Tronchet、Apparu-Turquois、Laroze、Seman

  DOI：——

  日期：——
• Pharmacophore and structure–activity relationships of integrase inhibition within a dual inhibitor scaffold of HIV reverse transcriptase and integrase
  作者：Zhengqiang Wang、Jing Tang、Christine E. Salomon、Christine D. Dreis、Robert Vince

  DOI：10.1016/j.bmc.2010.05.004

  日期：2010.6.15

  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.
• Synthesis of pyrimidine and quinolone conjugates as a scaffold for dual inhibitors of HIV reverse transcriptase and integrase
  作者：Zhengqiang Wang、Robert Vince

  DOI：10.1016/j.bmcl.2008.01.025

  日期：2008.2

  A series of conjugates combining a pyrimidine and a quinolone moiety were designed and synthesized. The assay results show that these compounds demonstrate both anti-RT activity and anti-IN activity and therefore provide a useful scaffold for identifying inhibitors with balanced dual activities. Published by Elsevier Ltd.