6-(4-hydroxybutylamino)-3-propyl-7H-purin-2-one | 195870-78-1

• 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: 6-(4-hydroxybutylamino)-3-propyl-7H-purin-2-one
• CAS: 195870-78-1
• 化学式: C₁₂H₁₉N₅O₂
• 分子量: 265.315
• InChiKey: OYUOQWXMDCUODU-UHFFFAOYSA-N

物化性质

• 沸点：
  541.6±56.0 °C(Predicted)
• 密度：
  1.38±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  19
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  93.6
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  6-(4-hydroxybutylamino)-3-propyl-7H-purin-2-one 在 potassium carbonate 、 甲基磺酰氯 、 三乙胺 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 8.0h， 生成 3,4-Dipropyl-3,4,6,7,8,9-hexahydro-1,3,4,5a,10-pentaaza-cyclohepta[e]inden-5-one
  参考文献：
  名称：

  Selective Inhibitors of Cyclic AMP-Specific Phosphodiesterase:  Heterocycle-Condensed Purines

  摘要：

  To reverse the adverse reactions of alkylxanthines and to develop novel inhibitors of cyclic AMP-specific phosphodiesterase (PDE IV), a series of heterocycle-condensed purines were designed and synthesized. Some of these new compounds had similar or more potent and selective inhibitory activity against PDE IV than known PDE IV inhibitors. The tracheal-relaxant activity of these compounds was closely correlated with their PDE IV-inhibitory activity. Moreover, these purine analogues did not have any positive-chronotropic action or adenosine-antagonistic action on isolated heart preparations, which are the particular adverse reactions of alkylxanthines. Among them, 3,4-dipropyl-4,5,7,8-tetrahydro-3H-imidazo[1,2-i]purin-5-one (1c), which was the most selective and potent PDE TV inhibitor, did not cause emesis in Suncus murinus at a dosage range of 10-100 mg/kg (po), while an imidazole analogue of 1c (4c) and known PDE IV inhibitors such as rolipram and denbufylline caused emesis even at 10 or 30 mg/kg.

  DOI：

  10.1021/jm970089s
• 作为产物：
  描述：

  6-氨基-3-丙基-7H-嘌呤-2-酮 在 吡啶 、 三甲基氯硅烷 、 三乙胺 作用下， 以 乙腈 为溶剂， 反应 20.0h， 生成 6-(4-hydroxybutylamino)-3-propyl-7H-purin-2-one
  参考文献：
  名称：

  Selective Inhibitors of Cyclic AMP-Specific Phosphodiesterase:  Heterocycle-Condensed Purines

  摘要：

  To reverse the adverse reactions of alkylxanthines and to develop novel inhibitors of cyclic AMP-specific phosphodiesterase (PDE IV), a series of heterocycle-condensed purines were designed and synthesized. Some of these new compounds had similar or more potent and selective inhibitory activity against PDE IV than known PDE IV inhibitors. The tracheal-relaxant activity of these compounds was closely correlated with their PDE IV-inhibitory activity. Moreover, these purine analogues did not have any positive-chronotropic action or adenosine-antagonistic action on isolated heart preparations, which are the particular adverse reactions of alkylxanthines. Among them, 3,4-dipropyl-4,5,7,8-tetrahydro-3H-imidazo[1,2-i]purin-5-one (1c), which was the most selective and potent PDE TV inhibitor, did not cause emesis in Suncus murinus at a dosage range of 10-100 mg/kg (po), while an imidazole analogue of 1c (4c) and known PDE IV inhibitors such as rolipram and denbufylline caused emesis even at 10 or 30 mg/kg.

  DOI：

  10.1021/jm970089s

文献信息

• Selective Inhibitors of Cyclic AMP-Specific Phosphodiesterase:  Heterocycle-Condensed Purines
  作者：Hiroyuki Sawanishi、Hirokazu Suzuki、Shinya Yamamoto、Yoshihiro Waki、Shohei Kasugai、Keiichi Ohya、Nagao Suzuki、Ken-ichi Miyamoto、Kenzo Takagi

  DOI：10.1021/jm970089s

  日期：1997.9.1

  To reverse the adverse reactions of alkylxanthines and to develop novel inhibitors of cyclic AMP-specific phosphodiesterase (PDE IV), a series of heterocycle-condensed purines were designed and synthesized. Some of these new compounds had similar or more potent and selective inhibitory activity against PDE IV than known PDE IV inhibitors. The tracheal-relaxant activity of these compounds was closely correlated with their PDE IV-inhibitory activity. Moreover, these purine analogues did not have any positive-chronotropic action or adenosine-antagonistic action on isolated heart preparations, which are the particular adverse reactions of alkylxanthines. Among them, 3,4-dipropyl-4,5,7,8-tetrahydro-3H-imidazo[1,2-i]purin-5-one (1c), which was the most selective and potent PDE TV inhibitor, did not cause emesis in Suncus murinus at a dosage range of 10-100 mg/kg (po), while an imidazole analogue of 1c (4c) and known PDE IV inhibitors such as rolipram and denbufylline caused emesis even at 10 or 30 mg/kg.