9-(2-hydroxypropyl)hypoxanthine | 75166-58-4

• 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: 9-(2-hydroxypropyl)hypoxanthine
• 英文别名: 9-(2-Hydroxy-1-propyl)hypoxanthine；9-(2-hydroxypropyl)-1H-purin-6-one
• CAS: 75166-58-4
• 化学式: C₈H₁₀N₄O₂
• 分子量: 194.193
• InChiKey: SDGOBZFXYQNSIM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.9
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  79.5
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  9-(2-hydroxypropyl)hypoxanthine 在 Varicella-Zoster thymidine kinase 、 magnesium 、 5’-三磷酸腺苷 作用下， 以 水 为溶剂， 反应 1.0h， 生成 Phosphoric acid mono-[1-methyl-2-(6-oxo-1,6-dihydro-purin-9-yl)-ethyl] ester
  参考文献：
  名称：

  Synthesis, Kinetics, and Molecular Docking of Novel 9-(2-Hydroxypropyl)purine Nucleoside Analogs as Ligands of Herpesviral Thymidine Kinases

  摘要：

  In the context of broadening the knowledge on substrate specificity of Herpes simplex virus type I thymidine kinase (HSV-1 TK) and Varicella-Zoster virus thymidine kinase (VZV TK), new derivatives of 9-(2-hydroxypropyl)-substituted adenine, chloropurine, hypoxanthine, guanine, thiopurine, and (methylsulfanyl)purine were synthesized and, subjected to in vitro phosphorylation and binding affinity assays. The interactions between the compounds and the crystallographically determined active site residues of HSV-1 TK have been studied by molecular modeling with the Lamarckian genetic algorithm of docking program AutoDock 3.0. All compounds mentioned bind to both enzymes in the low mm to sub-mM range, comparable to binding affinities of existing prodrugs. Findings from the docking procedure indicate multiple binding modes for all of the compounds and are in accordance with the results of phosphorylation and binding-affinity studies. Furthermore, the studies reveal that hypoxanthine derivatives represent a new class of TK substrates and thiopurine derivatives a new class of TK inhibitors.

  DOI：

  10.1002/1522-2675(200210)85:10<3237::aid-hlca3237>3.0.co;2-3
• 作为产物：
  描述：

  6-Chlor-9-<2-hydroxy-propyl>-purin 在 盐酸 作用下， 反应 2.0h， 以43%的产率得到9-(2-hydroxypropyl)hypoxanthine
  参考文献：
  名称：

  Synthesis, Kinetics, and Molecular Docking of Novel 9-(2-Hydroxypropyl)purine Nucleoside Analogs as Ligands of Herpesviral Thymidine Kinases

  摘要：

  In the context of broadening the knowledge on substrate specificity of Herpes simplex virus type I thymidine kinase (HSV-1 TK) and Varicella-Zoster virus thymidine kinase (VZV TK), new derivatives of 9-(2-hydroxypropyl)-substituted adenine, chloropurine, hypoxanthine, guanine, thiopurine, and (methylsulfanyl)purine were synthesized and, subjected to in vitro phosphorylation and binding affinity assays. The interactions between the compounds and the crystallographically determined active site residues of HSV-1 TK have been studied by molecular modeling with the Lamarckian genetic algorithm of docking program AutoDock 3.0. All compounds mentioned bind to both enzymes in the low mm to sub-mM range, comparable to binding affinities of existing prodrugs. Findings from the docking procedure indicate multiple binding modes for all of the compounds and are in accordance with the results of phosphorylation and binding-affinity studies. Furthermore, the studies reveal that hypoxanthine derivatives represent a new class of TK substrates and thiopurine derivatives a new class of TK inhibitors.

  DOI：

  10.1002/1522-2675(200210)85:10<3237::aid-hlca3237>3.0.co;2-3

文献信息

• 9-(Hydroxy alkyl)purines
  申请人：Newport Pharmaceuticals International, Inc.

  公开号：US04221910A1

  公开（公告）日：1980-09-09

  There are prepared compounds of the formula ##STR1## where X is OH, R.sup.2 is CH.sub.3 and R.sup.1 is alkyl of 1 to 8 carbon atoms. The compounds are immunopotentiators, have antiviral activity and anti-leukemic activity.

  有一些化合物的配方已经准备好了，该配方为：##STR1## 其中X为OH，R.sup.2为CH.sub.3，R.sup.1为1至8个碳原子的烷基。这些化合物是免疫增强剂，具有抗病毒活性和抗白血病活性。
• Complexes of 9-hydroxyalkyl-purines, processes for preparing them and therapeutical compositions containing the complexes as active ingredients
  申请人：Newport Pharmaceuticals International, Inc.

  公开号：EP0009154B1

  公开（公告）日：1982-12-08
• 9-Hydroxyalkyl-purines, processes for preparing them and therapeutical composition containing the 9-hydroxyalkyl-purines as active ingredients
  申请人：Newport Pharmaceuticals International, Inc.

  公开号：EP0009155B1

  公开（公告）日：1982-11-17
• US4221794A
  申请人：——

  公开号：US4221794A

  公开（公告）日：1980-09-09
• US4221910A
  申请人：——

  公开号：US4221910A

  公开（公告）日：1980-09-09