1,3,7-trimethyl-1H-imidazo[2,1-f]purine-2,4(3H,8H)-dione | 19977-26-5

• 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: 1,3,7-trimethyl-1H-imidazo[2,1-f]purine-2,4(3H,8H)-dione
• 英文别名: 1,3,7-trimethyl-1H,8H-imidazo[2,1-f]purine-2,4-dione；1,3,7-trimethyl-1H-imidazo[1,2-f]purine-2,4(3H,8H)-dione；2,4,7-trimethyl-6H-purino[7,8-a]imidazole-1,3-dione
• CAS: 19977-26-5
• 化学式: C₁₀H₁₁N₅O₂
• 分子量: 233.23
• InChiKey: UCRWKJWWUYKFAC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  17
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  73.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  1,3-dimethyl-8-amino-7-(2-oxopropyl)-3,7-dihydropurine-2,6-dione 在 溶剂黄146 作用下， 反应 4.0h， 以60%的产率得到1,3,7-trimethyl-1H-imidazo[2,1-f]purine-2,4(3H,8H)-dione
  参考文献：
  名称：

  Structure–activity relationship studies of a new series of imidazo[2,1-f]purinones as potent and selective A3 adenosine receptor antagonists

  摘要：

  We recently described the synthesis of 1-benzyl-3-propyl-1H,8H-imidazo[2,1-f]purine-2,4-diones, new potent and selective A(3) adenosine receptor antagonists containing a xanthine core. The present work can be considered an extension of our SAR studies on related structures in which the effect of different kind of substitutions at the 1-, 3- and 8-positions has been evaluated in order to improve both the potency and the hydrophilicity of the originally synthesised molecules. The A(3) binding disposition of these compounds was also investigated through docking and 3D-QSAR studies. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2008.10.049

文献信息

• Design, synthesis and molecular docking study of new purine derivatives as Aurora kinase inhibitors
  作者：Mohamed E. Khalifa

  DOI：10.1016/j.molstruc.2020.129843

  日期：2021.4

  Nine new purine-based compounds were designed and have been synthesized through series reactions of the starting compound 8-amino-substituted purine (2) with various reagents. Full characterizations of the synthesized compounds were performed to elucidate their chemical structures by means of physical and spectroscopic methods. All products were in-vitro tested for their potent anti-cancer action against

  设计了九种新的基于嘌呤的化合物，这些化合物是通过起始化合物8-氨基取代的嘌呤（2）与各种试剂的系列反应合成的。通过物理和光谱方法对合成的化合物进行了全面表征，以阐明其化学结构。所有产品均经过体外测试，证明它们对不同人类癌症具有有效的抗癌作用。白血病（HL60），肺癌（A549），乳腺癌（SKBR3）和胃癌（MKN45）。根据实验生物学评估，合成子尤其显示出对SKBR3细胞系的更高效率，因此与抗癌酶（极光激酶）对接以充分了解酶活性位点内部每个实体的联系。
• US7435740B2
  申请人：——

  公开号：US7435740B2

  公开（公告）日：2008-10-14
• Structure–activity relationship studies of a new series of imidazo[2,1-f]purinones as potent and selective A3 adenosine receptor antagonists
  作者：Pier Giovanni Baraldi、Delia Preti、Mojgan Aghazadeh Tabrizi、Romeo Romagnoli、Giulia Saponaro、Stefania Baraldi、Maurizio Botta、Cesare Bernardini、Andrea Tafi、Tiziano Tuccinardi

  DOI：10.1016/j.bmc.2008.10.049

  日期：2008.12.15

  We recently described the synthesis of 1-benzyl-3-propyl-1H,8H-imidazo[2,1-f]purine-2,4-diones, new potent and selective A(3) adenosine receptor antagonists containing a xanthine core. The present work can be considered an extension of our SAR studies on related structures in which the effect of different kind of substitutions at the 1-, 3- and 8-positions has been evaluated in order to improve both the potency and the hydrophilicity of the originally synthesised molecules. The A(3) binding disposition of these compounds was also investigated through docking and 3D-QSAR studies. (C) 2008 Elsevier Ltd. All rights reserved.