5,5'-bis[(6-chloro-9H-purin-9-yl)methyl]-4,4',5,5'-tetrahydro-1H,1'H-3,3'-bipyrazole | 1557969-27-3

• 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: 5,5'-bis[(6-chloro-9H-purin-9-yl)methyl]-4,4',5,5'-tetrahydro-1H,1'H-3,3'-bipyrazole
• 英文别名: 6-chloro-9-[[3-[5-[(6-chloropurin-9-yl)methyl]-4,5-dihydro-1H-pyrazol-3-yl]-4,5-dihydro-1H-pyrazol-5-yl]methyl]purine
• CAS: 1557969-27-3
• 化学式: C₁₈H₁₆Cl₂N₁₂
• 分子量: 471.311
• InChiKey: DMGNMMZUZFVLNV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  32
• 可旋转键数：
  5
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  136
• 氢给体数：
  2
• 氢受体数：
  10

反应信息

• 作为产物：
  描述：

  9-allyl-6-chloro-9H-purine 在 N-溴代丁二酰亚胺(NBS) 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 甲苯 、 苯 为溶剂， 反应 49.75h， 生成 6-chloro-9-{[1-(4-methylphenyl)-3-phenyl-1H-pyrazol-5-yl]methyl}-9H-purine 、 5,5'-bis[(6-chloro-9H-purin-9-yl)methyl]-4,4',5,5'-tetrahydro-1H,1'H-3,3'-bipyrazole
  参考文献：
  名称：

  Synthesis and biological evaluation of modified purine homo-N-nucleosides containing pyrazole or 2-pyrazoline moiety

  摘要：

  9-Substituted (pyrazol-5-yl)methyl- or (2-pyrazolin-5-yl)methyl-9H-purines were synthesized from 9-allyl-6-chloro-9H-purine through the 1,3-dipolar cycloaddition reaction with nitrile imines, prepared in situ from the corresponding hydrazone and NBS/Et3N under MW or from hydrazinoylchloride and Et3N under reflux. The coupling of new 6-chloropurines with amines in H2O under microwaves resulted quantitatively to modified pyrazol-5-yl- or 2-pyrazolin-5-yl adenine homo-N-nucleosides. The new compounds were tested in vitro for their ability to: (i) interact with 1,1-diphenyl-2-picryl-hydrazyl (DPPH), (ii) inhibit lipid peroxidation, (iii) inhibit the activity of soybean lipoxygenase, (iv) inhibit in vitro thrombin and for (v) their antiproliferative and cytotoxic activity. Pyrazolines were found to be more potent in vitro. Compound 7a exhibited satisfactory combined antioxidant and anti-lipid peroxidation activity, inhibition of lipoxygenase (89%) and thrombin inhibitory ability, whereas compound 7b exhibited high lipoxygenase inhibitory activity in combination to significant anti-thrombin activity. No compound exhibited a significant cytotoxic activity, while all showed moderate antiproliferative activity.

  DOI：

  10.3109/14756366.2012.755623

文献信息

• Synthesis and biological evaluation of modified purine homo-<i>N</i>-nucleosides containing pyrazole or 2-pyrazoline moiety
  作者：Andreas Thalassitis、Anna-Maria Katsori、Konstantinos Dimas、Dimitra J. Hadjipavlou-Litina、Fokion Pyleris、Nikolaos Sakellaridis、Konstantinos E. Litinas

  DOI：10.3109/14756366.2012.755623

  日期：2014.2.1

  9-Substituted (pyrazol-5-yl)methyl- or (2-pyrazolin-5-yl)methyl-9H-purines were synthesized from 9-allyl-6-chloro-9H-purine through the 1,3-dipolar cycloaddition reaction with nitrile imines, prepared in situ from the corresponding hydrazone and NBS/Et3N under MW or from hydrazinoylchloride and Et3N under reflux. The coupling of new 6-chloropurines with amines in H2O under microwaves resulted quantitatively to modified pyrazol-5-yl- or 2-pyrazolin-5-yl adenine homo-N-nucleosides. The new compounds were tested in vitro for their ability to: (i) interact with 1,1-diphenyl-2-picryl-hydrazyl (DPPH), (ii) inhibit lipid peroxidation, (iii) inhibit the activity of soybean lipoxygenase, (iv) inhibit in vitro thrombin and for (v) their antiproliferative and cytotoxic activity. Pyrazolines were found to be more potent in vitro. Compound 7a exhibited satisfactory combined antioxidant and anti-lipid peroxidation activity, inhibition of lipoxygenase (89%) and thrombin inhibitory ability, whereas compound 7b exhibited high lipoxygenase inhibitory activity in combination to significant anti-thrombin activity. No compound exhibited a significant cytotoxic activity, while all showed moderate antiproliferative activity.