N-[4-(5-hydroxy-2,4-dioxo-1,3-dipropyl-2,3,4,5-tetrahydro-1H-pyrrolo[3,2-d]pyrimidin-6-yl)-phenyl]-acetamide | 548943-40-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 英文名称: N-[4-(5-hydroxy-2,4-dioxo-1,3-dipropyl-2,3,4,5-tetrahydro-1H-pyrrolo[3,2-d]pyrimidin-6-yl)-phenyl]-acetamide
• 英文别名: N-[4-(5-hydroxy-2,4-dioxo-1,3-dipropylpyrrolo[3,2-d]pyrimidin-6-yl)phenyl]acetamide
• CAS: 548943-40-4
• 化学式: C₂₀H₂₄N₄O₄
• 分子量: 384.435
• InChiKey: DAWPGIWUAVNXAT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  28
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  94.9
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-[4-(5-hydroxy-2,4-dioxo-1,3-dipropyl-2,3,4,5-tetrahydro-1H-pyrrolo[3,2-d]pyrimidin-6-yl)-phenyl]-acetamide 在 sodium hydroxide 作用下， 以 乙醇 为溶剂， 反应 2.0h， 以51%的产率得到6-(4-amino-phenyl)-5-hydroxy-1,3-dipropyl-1H-pyrrolo[3,2-d]pyrimidine-2,4(3H,5H)-dione
  参考文献：
  名称：

  1,3-Dialkyl-8-(hetero)aryl-9-OH-9-deazaxanthines as potent A2B adenosine receptor antagonists: Design, synthesis, structure–affinity and structure–selectivity relationships

  摘要：

  A number of 1,3-dialkyl-8-(hetero)aryl-9-OH-9-deazaxanthines were prepared and evaluated as ligands of recombinant human adenosine receptors (hARs). Several 1,3-dipropyl derivatives endowed with nano-molar binding affinity at hA(2B) receptors, but poor selectivity over hA(2A), hA(1) and hA(3) AR subtypes were identified. A comparison with the corresponding 7-OH- and 7,9-unsubstituted-deazaxanthines revealed that 9-OH-9-deazaxanthines are more potent hA(2B) ligands with lower partition coefficients and higher water solubility compared to the other two congeneric classes of deazaxanthines. An optimization of the para-substituent of the 8-phenyl ring of 9-OH-9-deazaxanthines led to the discovery of compound 38, which exhibited outstanding hA(2B) affinity (Ki = 1.0 nM), good selectivity over hA(2A), hA(1) and hA(3) (selectivity indices = 100, 79 and 1290, respectively) and excellent antagonist potency in a functional assay on rat A(2B) (pA(2B) = 9.33). (C) 2008 Published by Elsevier Ltd.

  DOI：

  10.1016/j.bmc.2008.09.067
• 作为产物：
  描述：

  N-{4-[(E)-2-(5-Nitro-2,6-dioxo-1,3-dipropyl-1,2,3,6-tetrahydro-pyrimidin-4-yl)-vinyl]-phenyl}-acetamide 在 tin(ll) chloride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 N-[4-(5-hydroxy-2,4-dioxo-1,3-dipropyl-2,3,4,5-tetrahydro-1H-pyrrolo[3,2-d]pyrimidin-6-yl)-phenyl]-acetamide
  参考文献：
  名称：

  Fast and highly efficient one-pot synthesis of 9-deazaxanthines

  摘要：

  SnCl2 enables a direct, high-yield conversion of 5-nitro-1,3-dialkyl-6-styryl(furyl-, thienyl-vinyl)-uracils to 8-substituted-9-deazaxanthines under very mild experimental conditions. The method has a general applicability and it is compatible with the reactivity of the most common organic functional groups. In slightly experimental different conditions, it allows a high-yield and fast (<5 min) preparation of pure 7-N-hydroxy-9-deazaxanthines. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(03)00173-4