6-chloro-2-phenyl-9H-8-azapurine | 478629-91-3

• 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: 6-chloro-2-phenyl-9H-8-azapurine
• 英文别名: 7-Chloro-5-phenyl-2H-[1,2,3]triazolo[4,5-d]pyrimidine；7-chloro-5-phenyl-2H-triazolo[4,5-d]pyrimidine
• CAS: 478629-91-3
• 化学式: C₁₀H₆ClN₅
• 分子量: 231.644
• InChiKey: QBAPEWOXPUJUIF-UHFFFAOYSA-N

物化性质

• 密度：
  1.523±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  67.4
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-氨基壬烷-2-醇 、 6-chloro-2-phenyl-9H-8-azapurine 以 乙醇 为溶剂， 反应 15.0h， 以69%的产率得到
  参考文献：
  名称：

  erythro- and threo-2-Hydroxynonyl substituted 2-phenyladenines and 2-phenyl-8-azaadenines: ligands for A1 adenosine receptors and adenosine deaminase

  摘要：

  erythro-2-Phenyl-9-(2-hydroxy-3-nonyl)adenine and its 8-aza analog were prepared and showed a very high inhibitory activity towards adenosine deaminase (ADA), with K-i 0.55 and 1.67 nM, respectively, and high affinity for A, adenosine receptors, with K-i 28 and 2.8 nM, respectively. To increase affinity for A(1) receptors we introduced a substituent on the N-6 position such as alkyl or cycloalkyl groups, which are present in effective agonists or antagonists. Furthermore, for some compounds, we prepared the two diastereoisomers erythro and threo to verify whether the binding with A(1) receptors is stereoselective, as in ADA. Results show that some of the synthesised compounds are good inhibitors for ADA and good ligands for A(1), and the erythro diastereoisomers are more active than the threo ones. The experimental evidence allows us to hypothesise some similarity in the three dimensional structures of the binding site of the two proteins, ADA and A(1) adenosine receptor, in spite of lacking any homologies in the aminoacid sequences. (C) 2002 Editions scientifiques et medicales Elsevier SAS. All rights reserved.

  DOI：

  10.1016/s0014-827x(02)01200-4
• 作为产物：
  描述：

  4,6-二氯-5-硝基-2-苯基嘧啶 在 potassium nitrite 、 氨 、 铁粉 、 溶剂黄146 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 反应 78.5h， 生成 6-chloro-2-phenyl-9H-8-azapurine
  参考文献：
  名称：

  erythro- and threo-2-Hydroxynonyl substituted 2-phenyladenines and 2-phenyl-8-azaadenines: ligands for A1 adenosine receptors and adenosine deaminase

  摘要：

  erythro-2-Phenyl-9-(2-hydroxy-3-nonyl)adenine and its 8-aza analog were prepared and showed a very high inhibitory activity towards adenosine deaminase (ADA), with K-i 0.55 and 1.67 nM, respectively, and high affinity for A, adenosine receptors, with K-i 28 and 2.8 nM, respectively. To increase affinity for A(1) receptors we introduced a substituent on the N-6 position such as alkyl or cycloalkyl groups, which are present in effective agonists or antagonists. Furthermore, for some compounds, we prepared the two diastereoisomers erythro and threo to verify whether the binding with A(1) receptors is stereoselective, as in ADA. Results show that some of the synthesised compounds are good inhibitors for ADA and good ligands for A(1), and the erythro diastereoisomers are more active than the threo ones. The experimental evidence allows us to hypothesise some similarity in the three dimensional structures of the binding site of the two proteins, ADA and A(1) adenosine receptor, in spite of lacking any homologies in the aminoacid sequences. (C) 2002 Editions scientifiques et medicales Elsevier SAS. All rights reserved.

  DOI：

  10.1016/s0014-827x(02)01200-4

文献信息

• erythro- and threo-2-Hydroxynonyl substituted 2-phenyladenines and 2-phenyl-8-azaadenines: ligands for A1 adenosine receptors and adenosine deaminase
  作者：Giuliana Biagi、Irene Giorgi、Oreste Livi、Federica Pacchini、Pietro Rum、Valerio Scartoni、Barbara Costa、Maria Rosa Mazzoni、Laura Giusti

  DOI：10.1016/s0014-827x(02)01200-4

  日期：2002.3

  erythro-2-Phenyl-9-(2-hydroxy-3-nonyl)adenine and its 8-aza analog were prepared and showed a very high inhibitory activity towards adenosine deaminase (ADA), with K-i 0.55 and 1.67 nM, respectively, and high affinity for A, adenosine receptors, with K-i 28 and 2.8 nM, respectively. To increase affinity for A(1) receptors we introduced a substituent on the N-6 position such as alkyl or cycloalkyl groups, which are present in effective agonists or antagonists. Furthermore, for some compounds, we prepared the two diastereoisomers erythro and threo to verify whether the binding with A(1) receptors is stereoselective, as in ADA. Results show that some of the synthesised compounds are good inhibitors for ADA and good ligands for A(1), and the erythro diastereoisomers are more active than the threo ones. The experimental evidence allows us to hypothesise some similarity in the three dimensional structures of the binding site of the two proteins, ADA and A(1) adenosine receptor, in spite of lacking any homologies in the aminoacid sequences. (C) 2002 Editions scientifiques et medicales Elsevier SAS. All rights reserved.