(E)-4-(3-((6-amino-1,3-diethyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-5-yl)amino)-3-oxoprop-1-en-1-yl)-2-methoxyphenyl acetate | 1436428-54-4

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: (E)-4-(3-((6-amino-1,3-diethyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-5-yl)amino)-3-oxoprop-1-en-1-yl)-2-methoxyphenyl acetate
• 英文别名: [4-[(E)-3-[(4-amino-1,3-diethyl-2,6-dioxopyrimidin-5-yl)amino]-3-oxoprop-1-enyl]-2-methoxyphenyl] acetate
• CAS: 1436428-54-4
• 化学式: C₂₀H₂₄N₄O₆
• 分子量: 416.434
• InChiKey: RUECFVBMMWVYRY-CSKARUKUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  30
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  131
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (E)-4-(3-((6-amino-1,3-diethyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-5-yl)amino)-3-oxoprop-1-en-1-yl)-2-methoxyphenyl acetate 在 硫酸氢铵 、 lithium aluminium tetrahydride 、 六甲基二硅烷 、 potassium carbonate 、 sodium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 N,N-二甲基甲酰胺 、 丙酮 、 乙腈 为溶剂， 150.0 ℃ 、900.02 kPa 条件下， 反应 77.0h， 生成 (E)-4-(4-(2-(1,3-diethyl-7-methyl-2,6-dioxo-2,3,6,7-tetrahydro-1H-purin-8-yl)vinyl)-2-methoxyphenoxy)butanoic acid
  参考文献：
  名称：

  Novel adenosine A2A receptor ligands: A synthetic, functional and computational investigation of selected literature adenosine A2A receptor antagonists for extending into extracellular space

  摘要：

  Growing evidence has suggested a role in targeting the adenosine A(2A) receptor for the treatment of Parkinson's disease. The literature compounds KW 6002 (2) and ZM 241385 (5) were used as a starting point from which a series of novel ligands targeting the adenosine A(2A) receptor were synthesized and tested in a recombinant human adenosine A(2A) receptor functional assay. In order to further explore these molecules, we investigated the biological effects of assorted linkers attached to different positions on selected adenosine A(2A) receptor antagonists, and assessed their potential binding modes using molecular docking studies. The results suggest that linking from the phenolic oxygen of selected adenosine A(2A) receptor antagonists is relatively well tolerated due to the extension towards extracellular space, and leads to the potential of attaching further functionality from this position. Crown Copyright (C) 2013 Published by Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.03.070
• 作为产物：
  描述：

  阿魏酸 在 4-二甲氨基吡啶 、 氯化亚砜 作用下， 以 吡啶 、 二氯甲烷 、 甲苯 为溶剂， 反应 33.0h， 生成 (E)-4-(3-((6-amino-1,3-diethyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-5-yl)amino)-3-oxoprop-1-en-1-yl)-2-methoxyphenyl acetate
  参考文献：
  名称：

  Novel adenosine A2A receptor ligands: A synthetic, functional and computational investigation of selected literature adenosine A2A receptor antagonists for extending into extracellular space

  摘要：

  Growing evidence has suggested a role in targeting the adenosine A(2A) receptor for the treatment of Parkinson's disease. The literature compounds KW 6002 (2) and ZM 241385 (5) were used as a starting point from which a series of novel ligands targeting the adenosine A(2A) receptor were synthesized and tested in a recombinant human adenosine A(2A) receptor functional assay. In order to further explore these molecules, we investigated the biological effects of assorted linkers attached to different positions on selected adenosine A(2A) receptor antagonists, and assessed their potential binding modes using molecular docking studies. The results suggest that linking from the phenolic oxygen of selected adenosine A(2A) receptor antagonists is relatively well tolerated due to the extension towards extracellular space, and leads to the potential of attaching further functionality from this position. Crown Copyright (C) 2013 Published by Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.03.070