6-benzyl-1-(3-(4-fluorophenyl)propyl)-5-isopropylpyrimidine-2,4(1H,3H)-dione | 1281859-88-8

• 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: 6-benzyl-1-(3-(4-fluorophenyl)propyl)-5-isopropylpyrimidine-2,4(1H,3H)-dione
• 英文别名: 6-Benzyl-1-[3-(4-fluorophenyl)propyl]-5-propan-2-ylpyrimidine-2,4-dione
• CAS: 1281859-88-8
• 化学式: C₂₃H₂₅FN₂O₂
• 分子量: 380.462
• InChiKey: JYPKHFFXLUTSQA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  28
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  49.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  6-benzyl-1-(3-(4-fluorophenyl)propyl)-5-isopropylpyrimidine-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72%的产率得到6-benzyl-1-(3-(4-fluorophenyl)propyl)-3-hydroxy-5-isopropylpyrimidine-2,4(1H,3H)-dione
  参考文献：
  名称：

  3-Hydroxypyrimidine-2,4-diones as an Inhibitor Scaffold of HIV Integrase

  摘要：

  Integrase (IN) represents a clinically validated target for the development of antivirals against human immunodeficiency virus (HIV). Inhibitors with a novel structure core are essential for combating resistance associated with known IN inhibitors (IN Is). We have previously disclosed a novel dual inhibitor scaffold of HIV IN and reverse transcriptase (RT). Here we report the complete structure activity relationship (SAR), molecular modeling, and resistance profile of this inhibitor type on IN inhibition. These studies support an antiviral mechanism of dual inhibition against both IN and RT and validate 3-hydroxypyrimidine-2,4-diones as an IN inhibitor scaffold.

  DOI：

  10.1021/jm1014378
• 作为产物：
  描述：

  1-(乙氧基甲基)-6-(苯基甲基)-5-丙-2-基嘧啶-2,4-二酮 在 potassium carbonate 、 caesium carbonate 、 magnesium 、 溶剂黄146 、 三氟乙酸 作用下， 以 甲醇 、 水 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 8.5h， 生成 6-benzyl-1-(3-(4-fluorophenyl)propyl)-5-isopropylpyrimidine-2,4(1H,3H)-dione
  参考文献：
  名称：

  3-Hydroxypyrimidine-2,4-diones as an Inhibitor Scaffold of HIV Integrase

  摘要：

  Integrase (IN) represents a clinically validated target for the development of antivirals against human immunodeficiency virus (HIV). Inhibitors with a novel structure core are essential for combating resistance associated with known IN inhibitors (IN Is). We have previously disclosed a novel dual inhibitor scaffold of HIV IN and reverse transcriptase (RT). Here we report the complete structure activity relationship (SAR), molecular modeling, and resistance profile of this inhibitor type on IN inhibition. These studies support an antiviral mechanism of dual inhibition against both IN and RT and validate 3-hydroxypyrimidine-2,4-diones as an IN inhibitor scaffold.

  DOI：

  10.1021/jm1014378

文献信息

• 3-Hydroxypyrimidine-2,4-diones as an Inhibitor Scaffold of HIV Integrase
  作者：Jing Tang、Kasthuraiah Maddali、Mathieu Metifiot、Yuk Y. Sham、Robert Vince、Yves Pommier、Zhengqiang Wang

  DOI：10.1021/jm1014378

  日期：2011.4.14

  Integrase (IN) represents a clinically validated target for the development of antivirals against human immunodeficiency virus (HIV). Inhibitors with a novel structure core are essential for combating resistance associated with known IN inhibitors (IN Is). We have previously disclosed a novel dual inhibitor scaffold of HIV IN and reverse transcriptase (RT). Here we report the complete structure activity relationship (SAR), molecular modeling, and resistance profile of this inhibitor type on IN inhibition. These studies support an antiviral mechanism of dual inhibition against both IN and RT and validate 3-hydroxypyrimidine-2,4-diones as an IN inhibitor scaffold.