(E)-methyl 4-(2-(1,3-diethyl-7-methyl-2,6-dioxo-2,3,6,7-tetrahydro-1H-purin-8-yl)vinyl)-2-methoxybenzoate

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 咪唑并嘧啶类
• 英文名称: (E)-methyl 4-(2-(1,3-diethyl-7-methyl-2,6-dioxo-2,3,6,7-tetrahydro-1H-purin-8-yl)vinyl)-2-methoxybenzoate
• 英文别名: methyl 4-[(E)-2-(1,3-diethyl-7-methyl-2,6-dioxopurin-8-yl)ethenyl]-2-methoxybenzoate
• 化学式: C₂₁H₂₄N₄O₅
• 分子量: 412.445
• InChiKey: VMSGDBNSJPKGJI-PKNBQFBNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  30
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  94
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (E)-methyl 4-(2-(1,3-diethyl-7-methyl-2,6-dioxo-2,3,6,7-tetrahydro-1H-purin-8-yl)vinyl)-2-methoxybenzoate 在 水 、 lithium hydroxide 作用下， 以 四氢呋喃 为溶剂， 以73%的产率得到(E)-4-(2-(1,3-diethyl-7-methyl-2,6-dioxo-2,3,6,7-tetrahydro-1H-purin-8-yl)vinyl)-2-methoxybenzoic acid
  参考文献：
  名称：

  Design and evaluation of xanthine based adenosine receptor antagonists: Potential hypoxia targeted immunotherapies

  摘要：

  Molecular modeling techniques were applied to the design, synthesis and optimization of a new series of xanthine based adenosine A(2A) receptor antagonists. The optimized lead compound was converted to a PEG derivative and a functional in vitro bioassay used to confirm efficacy. Additionally, the PEGylated version showed enhanced aqueous solubility and was inert to photoisomerization, a known limitation of existing antagonists of this class. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2013.09.043
• 作为产物：
  描述：

  1,3-二乙基脲 在 sodium dithionite 、 氨 、 乙酸酐 、 亚硝酸 、 potassium carbonate 、 溶剂黄146 作用下， 以 水 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 48.0h， 生成 (E)-methyl 4-(2-(1,3-diethyl-7-methyl-2,6-dioxo-2,3,6,7-tetrahydro-1H-purin-8-yl)vinyl)-2-methoxybenzoate
  参考文献：
  名称：

  Design and evaluation of xanthine based adenosine receptor antagonists: Potential hypoxia targeted immunotherapies

  摘要：

  Molecular modeling techniques were applied to the design, synthesis and optimization of a new series of xanthine based adenosine A(2A) receptor antagonists. The optimized lead compound was converted to a PEG derivative and a functional in vitro bioassay used to confirm efficacy. Additionally, the PEGylated version showed enhanced aqueous solubility and was inert to photoisomerization, a known limitation of existing antagonists of this class. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2013.09.043

文献信息

• Design and evaluation of xanthine based adenosine receptor antagonists: Potential hypoxia targeted immunotherapies
  作者：Rhiannon Thomas、Joslynn Lee、Vincent Chevalier、Sara Sadler、Kaisa Selesniemi、Stephen Hatfield、Michail Sitkovsky、Mary Jo Ondrechen、Graham B. Jones

  DOI：10.1016/j.bmc.2013.09.043

  日期：2013.12

  Molecular modeling techniques were applied to the design, synthesis and optimization of a new series of xanthine based adenosine A(2A) receptor antagonists. The optimized lead compound was converted to a PEG derivative and a functional in vitro bioassay used to confirm efficacy. Additionally, the PEGylated version showed enhanced aqueous solubility and was inert to photoisomerization, a known limitation of existing antagonists of this class. (C) 2013 Elsevier Ltd. All rights reserved.