1,3-dipropyl-8-(6-chloro-3-pyridyl)xanthine | 156547-59-0

• 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: 1,3-dipropyl-8-(6-chloro-3-pyridyl)xanthine
• 英文别名: 1,3-dipropyl-8-(6-chloro-pyridin-3-yl)xanthine；8-(6-chloropyridin-3-yl)-1,3-dipropyl-7H-purine-2,6-dione
• CAS: 156547-59-0
• 化学式: C₁₆H₁₈ClN₅O₂
• 分子量: 347.804
• InChiKey: LFXCYVITBNVTHL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  24
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  82.2
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1,3-dipropyl-8-(6-chloro-3-pyridyl)xanthine 在 肼 作用下， 以 乙醇 为溶剂， 反应 16.0h， 生成 1,3-diethyl-8-[6-hydrazino-3-pyridyl]xanthine
  参考文献：
  名称：

  [EN] SUBSTITUTED 8-HETEROARYL XANTHINES
  [FR] XANTHINES DE 8-HETEROARYLE SUBSTITUEES

  摘要：

  公开号：

  WO2005021548A3
• 作为产物：
  描述：

  6-羟基烟酸 在 吡啶 、 sodium hydroxide 、 氯化亚砜 、 N,N-二甲基甲酰胺 作用下， 反应 4.0h， 生成 1,3-dipropyl-8-(6-chloro-3-pyridyl)xanthine
  参考文献：
  名称：

  Substituted 1,3-Dipropylxanthines as Irreversible Antagonists of A1 Adenosine Receptors

  摘要：

  This report describes the synthesis of 29 xanthines containing a chemoreactive chloroaryl beta-chloroethylamino, alpha,beta-unsaturated carbonyl bromoacetyl, 3-(fluorosulfonyl)benzoyl, or 4-(fluorosulfonyl)benzoyl group as part of an exocyclic 1-, 3-, or 8-substituent. The xanthines inhibited the binding of [H-3]-8-cyclopentyl-1,3-dipropylxanthine ([H-3]CPX) to the A(1) adenosine receptor (A(1)AR) of DDT1 MF2 cells at IC(50)s in the low-nanomolar to low-micromolar range. Seven of the 29 analogues irreversibly inhibited the binding of [H-3]CPX without changing the K-D of that ligand; five were 1,3-dipropylxantines having the following reactive groups as 8-substituents: (bromoacetamido)methyl (24), (bromoacetamido)ethyl (25), (bromoacetamido)propyl (26), [4-(fluorosulfonyl)benzamido]methyl (33) or 3-[[4-(fluorosulfonyl)benzoyl]oxy]cyclopentyl (42). Both 8-cyclopentyl-3-[3-[[4-(fluorosulfonyl)benzoyl]oxy]propyl]-1-propylxanthine (53) and 8-cyclopentyl-3-bis[3-[[4-(fluorosulfonyl)benzoyl]oxy]propyl]xanthine (55) inhibited [H-3]CPX binding irreversibly. Five of the ligands, including 26, 33 (IC50 = 49 mu M), and 53 (IC50 = 9 mu M), antagonized the binding of [H-3]NECA to the A(2a)AR of PC12 cells, but unlike binding to the A(1)AR, binding to the A(2a)AR was completely reversible. The potency of 33 (IC50 = 2 mu M, 72% loss of CPX binding at 1 mu M) and 53 (IC50 - 0.01 mu M, 74% loss of CPX binding at 0.05 mu M) and their seletivity for the A(1)AR suggest that those two ligands may be useful in studies of the structure and function of that receptor.

  DOI：

  10.1021/jm00043a010

文献信息

• Antagonists of A2B adenosine receptors for treatment of inflammatory bowel disease
  申请人：Sitaraman Shanthi V.

  公开号：US20080176845A1

  公开（公告）日：2008-07-24

  The present invention relates to method for treating inflammatory bowel disease that includes administration of an effective amount of an antagonist of A 2B adenosine receptors (ARs).

  本发明涉及一种治疗炎症性肠病的方法，包括给予足量的A2B腺苷受体（ARs）拮抗剂。
• Substituted 8-[6-amino-3-pyridyl]xanthines
  申请人：Wang Guoquan

  公开号：US20080004292A1

  公开（公告）日：2008-01-03

  The present invention provides substituted 8-[6-amino-3-pyridyl]xanthines and pharmaceutical compositions that are selective antagonists of A 2B adenosine receptors (ARs). These compounds and compositions are useful as pharmaceutical agents.

  本发明提供了取代的8-[6-氨基-3-吡啶基]黄嘌呤和选择性A2B腺苷受体（ARs）拮抗剂的制药组合物。这些化合物和组合物可用作药物代理。
• SUBSTITUTED 8-[6-AMINO-3PYRIDYL]XANTHINES
  申请人：Thompson Robert D.

  公开号：US20090163491A1

  公开（公告）日：2009-06-25

  The present invention provides substituted 8-[6-amino-3-pyridyl]xanthines and pharmaceutical compositions that are selective antagonists of A 2B adenosine receptors (ARs). These compounds and compositions are useful as pharmaceutical agents.

  本发明提供了替代8-[6-氨基-3-吡啶基]黄嘌呤和药物组成物，这些物质是A2B腺苷受体（ARs）的选择性拮抗剂。这些化合物和组成物可以作为药物剂量使用。
• Substituted 8-heteroaryl xanthines
  申请人：Wang Guoquan

  公开号：US20050065341A1

  公开（公告）日：2005-03-24

  The present invention provides compounds and pharmaceutical compositions that are selective antagonists of A 2B adenosine receptors (ARs). These compounds and compositions are useful as pharmaceutical agents.

  本发明提供了选择性拮抗A2B腺苷受体（ARs）的化合物和药物组合物。这些化合物和组合物可用作药物制剂。
• Derivatives of 8-substituted xanthines
  申请人：Wang Guoquan

  公开号：US20070249598A1

  公开（公告）日：2007-10-25

  The present invention provides compounds and pharmaceutical compositions that are selective antagonists of A 2B adenosine receptors (ARs). These compounds and compositions are useful as pharmaceutical agents.

  本发明提供了选择性拮抗A2B腺苷受体（ARs）的化合物和药物组合物。这些化合物和组合物可用作药物制剂。