4-Propyl-4,6,7,8-tetrahydro-1H-1,3,4,5a,9-pentaaza-cyclopenta[a]naphthalen-5-one | 195869-88-6

• 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: 4-Propyl-4,6,7,8-tetrahydro-1H-1,3,4,5a,9-pentaaza-cyclopenta[a]naphthalen-5-one
• 英文别名: 4-propyl-1,7,8,9-tetrahydropyrimido[2,1-f]purin-5-one
• CAS: 195869-88-6
• 化学式: C₁₁H₁₅N₅O
• 分子量: 233.273
• InChiKey: LIBCKYBPWNCEOY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  64.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  溴丙烷 、 4-Propyl-4,6,7,8-tetrahydro-1H-1,3,4,5a,9-pentaaza-cyclopenta[a]naphthalen-5-one 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以38%的产率得到3,4-Dipropyl-4,6,7,8-tetrahydro-3H-1,3,4,5a,9-pentaaza-cyclopenta[a]naphthalen-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：

  3-propyl-6-(1,2,4-triazol-4-yl)purine 在 甲基磺酰氯 、 三乙胺 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 8.0h， 生成 4-Propyl-4,6,7,8-tetrahydro-1H-1,3,4,5a,9-pentaaza-cyclopenta[a]naphthalen-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

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.