1-[4-(Furan-2-yl)-11-methyl-3,5,6,8,10,11-hexazatricyclo[7.3.0.02,6]dodeca-1(12),2,4,7,9-pentaen-7-yl]-3-pyridin-2-ylurea | 881404-08-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 三唑并嘧啶类
• 英文名称: 1-[4-(Furan-2-yl)-11-methyl-3,5,6,8,10,11-hexazatricyclo[7.3.0.02,6]dodeca-1(12),2,4,7,9-pentaen-7-yl]-3-pyridin-2-ylurea
• CAS: 881404-08-6
• 化学式: C₁₇H₁₃N₉O₂
• 分子量: 375.349
• InChiKey: YFKPFCQGQVDYJK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  28
• 可旋转键数：
  3
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  128
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  1-[4-(Furan-2-yl)-11-methyl-3,5,6,8,10,11-hexazatricyclo[7.3.0.02,6]dodeca-1(12),2,4,7,9-pentaen-7-yl]-3-pyridin-2-ylurea 在 间氯过氧苯甲酸 作用下， 以 四氢呋喃 为溶剂， 反应 12.0h， 以78%的产率得到1-(2-Furan-2-yl-8-methyl-8H-pyrazolo[4,3-e][1,2,4]triazolo[1,5-c]pyrimidin-5-yl)-3-(1-oxy-pyridin-2-yl)-urea
  参考文献：
  名称：

  Synthesis and Biological Studies of a New Series of 5-Heteroarylcarbamoylaminopyrazolo[4,3-e]1,2,4-triazolo[1,5-c]pyrimidines as Human A₃ Adenosine Receptor Antagonists. Influence of the Heteroaryl Substituent on Binding Affinity and Molecular Modeling Investigations

  摘要：

  Some pyrazolotriazolopyrimidines bearing different heteroarylcarbamoylamino moieties at the N5-position are described. We previously reported the synthesis of a water soluble compound with high potency and selectivity versus the human A(3) adenosine receptor as antagonist, and herein we present an enlarged series of compounds related to the previously mentioned one. These compounds showed A(3) adenosine receptor affinity in the nanomolar range and different levels of selectivity evaluated in radioligand binding assays at human A(1), A(2)A, A(2B), and A(3) adenosine receptors. In particular, the effect of the heteroaryl substituents at the N5 position has been analyzed. This study allows us to recognize that the presence of a pyridinium moiety in this position not only increases water solubility but also improves or retains potency and selectivity at the human A(3) adenosine receptors. In contrast, replacement of pyridine with different heterocycles produces loss of affinity and selectivity at the human A(3) adenosine receptors. A molecular modeling study has been carried out with the aim to explain these various binding profiles.

  DOI：

  10.1021/jm051147+
• 作为产物：
  描述：

  吡啶-2-羰基叠氮化物 、 2-(2-furyl)-8-methyl-8H-pyrazolo[4,3-e][1,2,4]triazolo[1,5-c]pyrimidin-5-amine 以 1,4-二氧六环 为溶剂， 反应 18.0h， 以64%的产率得到1-[4-(Furan-2-yl)-11-methyl-3,5,6,8,10,11-hexazatricyclo[7.3.0.02,6]dodeca-1(12),2,4,7,9-pentaen-7-yl]-3-pyridin-2-ylurea
  参考文献：
  名称：

  Synthesis and Biological Studies of a New Series of 5-Heteroarylcarbamoylaminopyrazolo[4,3-e]1,2,4-triazolo[1,5-c]pyrimidines as Human A₃ Adenosine Receptor Antagonists. Influence of the Heteroaryl Substituent on Binding Affinity and Molecular Modeling Investigations

  摘要：

  Some pyrazolotriazolopyrimidines bearing different heteroarylcarbamoylamino moieties at the N5-position are described. We previously reported the synthesis of a water soluble compound with high potency and selectivity versus the human A(3) adenosine receptor as antagonist, and herein we present an enlarged series of compounds related to the previously mentioned one. These compounds showed A(3) adenosine receptor affinity in the nanomolar range and different levels of selectivity evaluated in radioligand binding assays at human A(1), A(2)A, A(2B), and A(3) adenosine receptors. In particular, the effect of the heteroaryl substituents at the N5 position has been analyzed. This study allows us to recognize that the presence of a pyridinium moiety in this position not only increases water solubility but also improves or retains potency and selectivity at the human A(3) adenosine receptors. In contrast, replacement of pyridine with different heterocycles produces loss of affinity and selectivity at the human A(3) adenosine receptors. A molecular modeling study has been carried out with the aim to explain these various binding profiles.

  DOI：

  10.1021/jm051147+

文献信息

• Synthesis and Biological Studies of a New Series of 5-Heteroarylcarbamoylaminopyrazolo[4,3-<i>e</i>]1,2,4-triazolo[1,5-<i>c</i>]pyrimidines as Human A₃ Adenosine Receptor Antagonists. Influence of the Heteroaryl Substituent on Binding Affinity and Molecular Modeling Investigations
  作者：Giorgia Pastorin、Tatiana Da Ros、Chiara Bolcato、Christian Montopoli、Stefano Moro、Barbara Cacciari、Pier Giovanni Baraldi、Katia Varani、Pier Andrea Borea、Giampiero Spalluto

  DOI：10.1021/jm051147+

  日期：2006.3.1

  Some pyrazolotriazolopyrimidines bearing different heteroarylcarbamoylamino moieties at the N5-position are described. We previously reported the synthesis of a water soluble compound with high potency and selectivity versus the human A(3) adenosine receptor as antagonist, and herein we present an enlarged series of compounds related to the previously mentioned one. These compounds showed A(3) adenosine receptor affinity in the nanomolar range and different levels of selectivity evaluated in radioligand binding assays at human A(1), A(2)A, A(2B), and A(3) adenosine receptors. In particular, the effect of the heteroaryl substituents at the N5 position has been analyzed. This study allows us to recognize that the presence of a pyridinium moiety in this position not only increases water solubility but also improves or retains potency and selectivity at the human A(3) adenosine receptors. In contrast, replacement of pyridine with different heterocycles produces loss of affinity and selectivity at the human A(3) adenosine receptors. A molecular modeling study has been carried out with the aim to explain these various binding profiles.