6-chloro-3,7-dipropylxanthine | 195870-46-3

• 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: 6-chloro-3,7-dipropylxanthine
• 英文别名: 6-Chloro-3,7-dipropylpurin-2-one
• CAS: 195870-46-3
• 化学式: C₁₁H₁₅ClN₄O
• 分子量: 254.719
• InChiKey: LMJIGECGRJRUDY-UHFFFAOYSA-N

物化性质

• 沸点：
  446.3±37.0 °C(Predicted)
• 密度：
  1.35±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  50.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  6-chloro-3,7-dipropylxanthine 在 ammonium hydroxide 作用下， 以 乙醇 为溶剂， 反应 12.0h， 以66%的产率得到6-amino-3,7-dipropylpurin-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
• 作为产物：
  描述：

  3,7-Dipropylxanthine 在 三氯氧磷 作用下， 反应 2.0h， 以92%的产率得到6-chloro-3,7-dipropylxanthine
  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

• Synthesis and Cyclic AMP Phosphodiesterase 4 Isoenzyme Inhibitory Activity of Heterocycle Condensed Purines.
  作者：Hirokazu Suzuki、Manabu Yamamoto、Susumu Shimura、Ken-ichi Miyamoto、Kenji Yamamoto、Hiroyuki Sawanishi

  DOI：10.1248/cpb.50.1163

  日期：——

  To reverse the adverse reactions of alkylxanthines and to develop novel inhibitors of cyclic AMP phosphodiesterase 4 (PDE4), a series of heterocycle [a]-, [b]-, [c,d]-, and [i]-condensed purines were designed and synthesized. Although all compounds did not display PDE1 and PDE3 inhibitory activities, several heterocycle [i]-condensed purines strongly inhibited PDE4. Especially, dl-3,4-dipropyl-8-methyl-4,5,7,8-tetrahydro-1H-imidazo[2,1-i]purin-5-one (dl-7c) exhibited comparable PDE4 inhibitory activity (IC50=1.9 μM) to rolipram and denbufylline (DBF).

  为了逆转烷基黄嘌呤的不良反应并开发新型环磷酸腺苷磷酸二酯酶4（PDE4）抑制剂，设计并合成了一系列杂环[a]-、[b]-、[c,d]-和[i]-稠合嘌呤。尽管所有化合物均未表现出PDE1和PDE3抑制活性，但几种杂环[i]-稠合嘌呤对PDE4表现出强烈抑制作用。特别是dl-3,4-二丙基-8-甲基-4,5,7,8-四氢-1H-咪唑并[2,1-i]嘌呤-5-酮（dl-7c）显示出与罗利普兰和丹布非林（DBF）相当的PDE4抑制活性（IC50=1.9 μM）。
• 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.