7-benzyl-1,2,3,4-tetrazolo[5,1-i]purine | 10553-44-3

• 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: 7-benzyl-1,2,3,4-tetrazolo[5,1-i]purine
• 英文别名: 7-benzyl-7H-tetrazolo[5,1-i]purine；7-Benzyl-7H-tetrazolo<5,1-i>purin；7H-Tetrazolo[5,1-i]purine, 7-benzyl-；7-benzyltetrazolo[5,1-f]purine
• CAS: 10553-44-3
• 化学式: C₁₂H₉N₇
• 分子量: 251.25
• InChiKey: HOHUVIRJDOLSQB-UHFFFAOYSA-N

物化性质

• 密度：
  1.60±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  73.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  9-benzyl-6-hydrazino-9H-purine 在 盐酸 、 sodium nitrite 作用下， 以 水 为溶剂， 反应 2.0h， 生成 7-benzyl-1,2,3,4-tetrazolo[5,1-i]purine
  参考文献：
  名称：

  Synthesis and evaluation of anticonvulsant and antidepressant activities of 7-alkyl-7H-tetrazolo[1,5-g]purine derivatives

  摘要：

  Seventeen 7-alkyl-7H-tetrazolo[1,5-g]purine derivatives were synthesized, and their anticonvulsant and antidepressant activities were evaluated in a mouse model. The anticonvulsant effect and neurotoxicity of the compounds were evaluated with a maximal electroshock test and a rotated test in mice, respectively. Most of the compounds had anticonvulsant activity; among the compounds studied, 7-(3-chlorobenzyl)-7H-tetrazolo[1,5-g]purine (3h) was found to be the most potent compound with a median effective dose (ED50) value of 28.9 mg/kg and a protective index value of 15.8, possessing better anticonvulsant activity and higher safety than the marketed drug carbamazepine. To explain the possible mechanism of anticonvulsant activity, compound 3h was tested in pentylenetetrazole-induced seizures tests, and the results suggest that compound 3h exerts anticonvulsant activity through a GABA-mediated mechanism. Forced swimming test showed that at a dose of 40 mg/kg, five compounds have significant antidepressant activity, the most active compound was 7-(2-chlorobenzyl)-7H-tetrazolo[1,5-g]purine (3g), which decreased immobility time by 56 %.

  DOI：

  10.1007/s00044-014-1030-0

文献信息

• Chattopadhyay, Gautam; Ray, Parlha Sinha, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2013, vol. 52, # 4, p. 546 - 552
  作者：Chattopadhyay, Gautam、Ray, Parlha Sinha

  DOI：——

  日期：——
• Synthesis and evaluation of anticonvulsant and antidepressant activities of 7-alkyl-7H-tetrazolo[1,5-g]purine derivatives
  作者：Shi-Ben Wang、Xian-Qing Deng、Da-Chuan Liu、Hong-Jian Zhang、Zhe-Shan Quan

  DOI：10.1007/s00044-014-1030-0

  日期：2014.10

  Seventeen 7-alkyl-7H-tetrazolo[1,5-g]purine derivatives were synthesized, and their anticonvulsant and antidepressant activities were evaluated in a mouse model. The anticonvulsant effect and neurotoxicity of the compounds were evaluated with a maximal electroshock test and a rotated test in mice, respectively. Most of the compounds had anticonvulsant activity; among the compounds studied, 7-(3-chlorobenzyl)-7H-tetrazolo[1,5-g]purine (3h) was found to be the most potent compound with a median effective dose (ED50) value of 28.9 mg/kg and a protective index value of 15.8, possessing better anticonvulsant activity and higher safety than the marketed drug carbamazepine. To explain the possible mechanism of anticonvulsant activity, compound 3h was tested in pentylenetetrazole-induced seizures tests, and the results suggest that compound 3h exerts anticonvulsant activity through a GABA-mediated mechanism. Forced swimming test showed that at a dose of 40 mg/kg, five compounds have significant antidepressant activity, the most active compound was 7-(2-chlorobenzyl)-7H-tetrazolo[1,5-g]purine (3g), which decreased immobility time by 56 %.

表征谱图