2-chloro-6-benzylamino-9-[1-(pentafluorobenzyl)-1H-1,2,3-triazol-4-yl-methyl]purine | 1314172-36-5

• 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: 2-chloro-6-benzylamino-9-[1-(pentafluorobenzyl)-1H-1,2,3-triazol-4-yl-methyl]purine
• 英文别名: 2-chloro-6-benzylamino-9-[(1-(2,3,4,5,6-pentafluorobenzyl)-1H-1,2,3-triazol-4-yl)methyl]purine；N-benzyl-2-chloro-9-[[1-[(2,3,4,5,6-pentafluorophenyl)methyl]triazol-4-yl]methyl]purin-6-amine
• CAS: 1314172-36-5
• 化学式: C₂₂H₁₄ClF₅N₈
• 分子量: 520.852
• InChiKey: JVRUYDSFAQOGBM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  36
• 可旋转键数：
  7
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  86.3
• 氢给体数：
  1
• 氢受体数：
  11

反应信息

• 作为产物：
  描述：

  α-溴-2,3,4,5,6-五氟甲基苯酸酯 在 sodium azide 、 copper(I) bromide 作用下， 以 二甲基亚砜 为溶剂， 反应 0.75h， 生成 2-chloro-6-benzylamino-9-[1-(pentafluorobenzyl)-1H-1,2,3-triazol-4-yl-methyl]purine
  参考文献：
  名称：

  Novel purine-based fluoroaryl-1,2,3-triazoles as neuroprotecting agents: Synthesis, neuronal cell culture investigations, and CDK5 docking studies

  摘要：

  A series of novel purine-based fluoroaryl triazoles were synthesized using the Cu(I) catalyzed 1,3-dipolar cycloaddition reactions (click reactions), and assayed for their neuroprotective effects using fluorescence electron microscopy. Among these triazoles, o-fluorophenylmetyl-triazole, 7, has comparable neuroprotective effect as that of Flavopiridol (1) and Roscovitine (2), the state of the art CDK inhibitors, against the Ab induced neurotoxicity. These results are substantiated using computer docking methods (DarwinDock/GenDock), which predict that Roscovitine and the triazole 7 bind to the ATP-binding site of CDK5/p25 with comparable binding energies, whereas the corresponding pentafluorophenylmethyl-triazole, 9, has dramatically reduced binding energy (in accordance with its lack of neuroprotection). These combined experimental and theoretical studies support the involvement of CDK5/p25 in the neuronal cell cycle re-entry. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.05.019

文献信息

• PURINE-BASED TRIAZOLES
  申请人：Casadesus Gemma

  公开号：US20140045866A1

  公开（公告）日：2014-02-13

  A pharmaceutical composition for inhibiting at least protein kinase in a cell of a subject includes a purine based triazole.

  一种用于抑制受试者细胞内至少一种蛋白激酶的药物组合物，包括一种以嘌呤为基础的三唑。
• US8969556B2
  申请人：——

  公开号：US8969556B2

  公开（公告）日：2015-03-03
• Novel purine-based fluoroaryl-1,2,3-triazoles as neuroprotecting agents: Synthesis, neuronal cell culture investigations, and CDK5 docking studies
  作者：Nanditha Nair、Wataru Kudo、Mark A. Smith、Ravinder Abrol、William A. Goddard、V. Prakash Reddy

  DOI：10.1016/j.bmcl.2011.05.019

  日期：2011.7

  A series of novel purine-based fluoroaryl triazoles were synthesized using the Cu(I) catalyzed 1,3-dipolar cycloaddition reactions (click reactions), and assayed for their neuroprotective effects using fluorescence electron microscopy. Among these triazoles, o-fluorophenylmetyl-triazole, 7, has comparable neuroprotective effect as that of Flavopiridol (1) and Roscovitine (2), the state of the art CDK inhibitors, against the Ab induced neurotoxicity. These results are substantiated using computer docking methods (DarwinDock/GenDock), which predict that Roscovitine and the triazole 7 bind to the ATP-binding site of CDK5/p25 with comparable binding energies, whereas the corresponding pentafluorophenylmethyl-triazole, 9, has dramatically reduced binding energy (in accordance with its lack of neuroprotection). These combined experimental and theoretical studies support the involvement of CDK5/p25 in the neuronal cell cycle re-entry. (C) 2011 Elsevier Ltd. All rights reserved.