8-cyclopentyl-1,3-diallylxanthine | 107464-75-5

• 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: 8-cyclopentyl-1,3-diallylxanthine
• 英文别名: 8-cyclopentyl-3,7-dihydro-1,3-bis(2-propenyl)-1H-purine-2,6-dione；8-cyclopentyl-1,3-bis(prop-2-en-1-yl)-2,3,6,7-tetrahydro-1H-purine-2,6-dione；8-cyclopentyl-1,3-bis(prop-2-enyl)-7H-purine-2,6-dione
• CAS: 107464-75-5
• 化学式: C₁₆H₂₀N₄O₂
• 分子量: 300.36
• InChiKey: NFJWUJHASSHJIF-UHFFFAOYSA-N

物化性质

• 沸点：
  541.5±60.0 °C(Predicted)
• 密度：
  1.227±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  69.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  8-cyclopentyl-1,3-diallylxanthine 在 sodium hydroxide 、 9-borabicyclo[3.3.1]nonane dimer 、 双氧水 作用下， 以 1,4-二氧六环 为溶剂， 反应 18.0h， 生成 8-cyclopentyl-1,3-(3-{[4-(fluorosulfonyl)benzoyl]oxy}propyl)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
• 作为产物：
  描述：

  N-[3-(dimethylamino)propyl]-4-(2,3,6,7-tetrahydro-2,6-dioxo-1,3-di-2-propenyl-1H-purine-8-yl)benzenesulfonamide 、 盐酸 生成 8-cyclopentyl-1,3-diallylxanthine
  参考文献：
  名称：

  Dialkenyl derivatives of xanthine, pharmaceutical compositions and

  摘要：

  本发明涉及多种新型咖啡因的二烯丙基类似物。此外，本发明还涉及以二烯丙基咖啡因类似物为活性化合物的制药组合物及其使用方法。本发明还涉及制备二烯丙基咖啡因类似物的方法。类似物的使用特别涉及对腺苷受体（特别是A.sub.1受体）的亲和力。类似物是腺苷受体拮抗剂。例如，类似物可提供用作中枢神经系统刺激剂、认知激活剂、抗心颤药和支气管扩张剂的活性。

  公开号：

  US04772607A1

文献信息

• Scammells Peter J., Baker Stephen P., Belardinelli Luiz, Olsson Ray A., J. Med. Chem, 37 (1994) N 17, S 2704-2712
  作者：Scammells Peter J., Baker Stephen P., Belardinelli Luiz, Olsson Ray A.

  DOI：——

  日期：——
• US4772607A
  申请人：——

  公开号：US4772607A

  公开（公告）日：1988-09-20