3,7-Dipropylxanthine | 135462-21-4

• 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: 3,7-Dipropylxanthine
• 英文别名: 3,7-Dipropyl-3,7-dihydro-1H-purine-2,6-dione；3,7-dipropylpurine-2,6-dione
• CAS: 135462-21-4
• 化学式: C₁₁H₁₆N₄O₂
• 分子量: 236.274
• InChiKey: PAFAWJVFVCLETB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 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：
  67.2
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3,7-Dipropylxanthine 在 ammonium hydroxide 、 三氯氧磷 作用下， 以 乙醇 为溶剂， 反应 14.0h， 生成 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：

  6-amino-5-formamido-1-n-propyl-2,4-(1H,3H)-pyrimidinedione 在 sodium hydroxide 、 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.5h， 生成 3,7-Dipropylxanthine
  参考文献：
  名称：

  黄嘌呤骨架的烷基取代对支气管扩张的影响。

  摘要：

  用豚鼠研究了一系列1,3,7-三烷基黄嘌呤的结构活性关系。在黄嘌呤骨架的1位和3位上，气管肌肉的松弛作用随烷基链长度的增加而增加，但在7位上的烷基化则减少。右心房的正变时性作用增强了3-烷基链的长度，但倾向于随着1-烷基化而减少，被7取代减弱。因此，尽管1和3取代对于气管平滑肌松弛同样重要，但对于支气管选择性，在1位置的取代比3取代更重要。7-烷基化对于消除心脏刺激可能很重要。在3个取代基中，平滑肌松弛作用与环状AMP-PDE抑制活性之间存在良好的相关性；在1、3和7个取代基中，其对腺苷（A1）受体的亲和力也良好。这表明，不仅环AMP-PDE抑制活性而且腺苷拮抗活性在烷基黄嘌呤的支气管扩张作用中也很重要。在这些黄嘌呤衍生物中，1-丁-3-丙基黄嘌呤及其7-甲基化衍生物在体外和体内实验中显示出比茶碱和Enprofylline高的支气管选择性，可能是支气管扩张剂的新候选者。这表明，不仅环AMP

  DOI：

  10.1021/jm00100a008

文献信息

• Xanthine derivative inhibitors of BET proteins
  申请人：Centre national de la recherche scientifique

  公开号：US11225481B2

  公开（公告）日：2022-01-18

  This invention relates to xanthine derivative compounds that are inhibitors of BET bromodomains proteins, the method of preparation thereof and applications thereof.

  本发明涉及作为 BET 溴链蛋白抑制剂的黄嘌呤衍生物化合物、其制备方法及其应用。
• XANTHINE DERIVATIVE INHIBITORS OF BET PROTEINS
  申请人：Centre national de la recherche scientifique

  公开号：US20190292186A1

  公开（公告）日：2019-09-26

  This invention relates to xanthine derivative compounds that are inhibitors of BET bromodomains proteins, the method of preparation thereof and applications thereof.
• [EN] HETEROCYCLIC COMPOUNDS AS ADENOSINE RECEPTOR ANTAGONIST<br/>[FR] COMPOSÉS HÉTÉROCYCLIQUES UTILES COMME ANTAGONISTES DES RÉCEPTEURS ADÉNOSINIQUES
  申请人：ADVINUS THERAPEUTICS PVT LTD

  公开号：WO2009118759A2

  公开（公告）日：2009-10-01

  Compounds of the present disclosure are fused pyrimidine compounds of formula (I), its tautomers, polymorphs, stereoisomers, prodrugs, solvate or a pharmaceutically acceptable salts thereof, as Adenosine receptor antagonists. Processes of their preparation are also described in the disclosure.
• 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.
• Effects of alkyl substitutions of xanthine skeleton on bronchodilation
  作者：Ryosuke Sakai、Kayo Konno、Yasunori Yamamoto、Fujiko Sanae、Kenzo Takagi、Takaaki Hasegawa、Nobuhiko Iwasaki、Masato Kakiuchi、Hideo Kato、Kenichi Miyamoto

  DOI：10.1021/jm00100a008

  日期：1992.10

  AMP-PDE inhibitory activity in 3-substituents and the affinity for adenosine (A1) receptors in 1-, 3-, and 7-substituents. This suggests that not only the cyclic AMP-PDE inhibitory activity but also the adenosine antagonistic activity is important in the bronchodilatory effects of alkylxanthines. Among these xanthine derivatives, 1-butyl-3-propylxanthine and its 7-methylated derivative showed high bronchoselectivity

  用豚鼠研究了一系列1,3,7-三烷基黄嘌呤的结构活性关系。在黄嘌呤骨架的1位和3位上，气管肌肉的松弛作用随烷基链长度的增加而增加，但在7位上的烷基化则减少。右心房的正变时性作用增强了3-烷基链的长度，但倾向于随着1-烷基化而减少，被7取代减弱。因此，尽管1和3取代对于气管平滑肌松弛同样重要，但对于支气管选择性，在1位置的取代比3取代更重要。7-烷基化对于消除心脏刺激可能很重要。在3个取代基中，平滑肌松弛作用与环状AMP-PDE抑制活性之间存在良好的相关性；在1、3和7个取代基中，其对腺苷（A1）受体的亲和力也良好。这表明，不仅环AMP-PDE抑制活性而且腺苷拮抗活性在烷基黄嘌呤的支气管扩张作用中也很重要。在这些黄嘌呤衍生物中，1-丁-3-丙基黄嘌呤及其7-甲基化衍生物在体外和体内实验中显示出比茶碱和Enprofylline高的支气管选择性，可能是支气管扩张剂的新候选者。这表明，不仅环AMP