8-(aminomethyl)-1,3-dipropyl-1H,3H,7H-purine-2,4-dione | 155930-28-2

• 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-(aminomethyl)-1,3-dipropyl-1H,3H,7H-purine-2,4-dione
• 英文别名: 8-(aminomethyl)-1,3-dipropylxanthine；8-(aminomethyl)-1,3-dipropyl-7H-purine-2,6-dione
• CAS: 155930-28-2
• 化学式: C₁₂H₁₉N₅O₂
• 分子量: 265.315
• InChiKey: QYQGVZMBGALLFP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  95.3
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  8-(aminomethyl)-1,3-dipropyl-1H,3H,7H-purine-2,4-dione 在 sodium hydride 、 溶剂黄146 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 5.0h， 生成 1,3-dipropyl-8,9-dihydro-1H,3H,6H-pyrazino<2,1-f>purine-2,4,7-trione
  参考文献：
  名称：

  新的[ f ]融合的黄嘌呤：1,3-二丙基-1 H，3 H-吡嗪，吡啶基，嘧啶基和吡咯并[2,1 - f ]嘌呤-2,4-二酮的合成

  摘要：

  从5,6-二氨基-1,3-二丙基嘧啶-开始，合成1,3-二丙基-1 H，3 H-吡嗪并，吡啶基，嘧啶基和吡咯并[2,1 - f ]嘌呤-2,4-二酮。描述了2，4-二酮1和6-氯-1，3-二丙基嘧啶-2，4-二酮14。1,3-二丙基-1 H，3 H-吡啶（或吡嗪并）[1'，2'-1,2]嘧啶[4,5 - d ]嘧啶-2,4,5-三酮的合成新方法还开发了19 e，f，h。

  DOI：

  10.1002/jhet.5570310115
• 作为产物：
  描述：

  8-<(2-carboxybenzamido)methyl>-1,3-dipropyl-1H,3H,7H-purine-2,4-dione 在 sodium hydroxide 作用下， 反应 3.0h， 以83%的产率得到8-(aminomethyl)-1,3-dipropyl-1H,3H,7H-purine-2,4-dione
  参考文献：
  名称：

  新的[ f ]融合的黄嘌呤：1,3-二丙基-1 H，3 H-吡嗪，吡啶基，嘧啶基和吡咯并[2,1 - f ]嘌呤-2,4-二酮的合成

  摘要：

  从5,6-二氨基-1,3-二丙基嘧啶-开始，合成1,3-二丙基-1 H，3 H-吡嗪并，吡啶基，嘧啶基和吡咯并[2,1 - f ]嘌呤-2,4-二酮。描述了2，4-二酮1和6-氯-1，3-二丙基嘧啶-2，4-二酮14。1,3-二丙基-1 H，3 H-吡啶（或吡嗪并）[1'，2'-1,2]嘧啶[4,5 - d ]嘧啶-2,4,5-三酮的合成新方法还开发了19 e，f，h。

  DOI：

  10.1002/jhet.5570310115

文献信息

• Substituted 1,3-Dipropylxanthines as Irreversible Antagonists of A1 Adenosine Receptors
  作者：Peter J. Scammells、Stephen P. Baker、Luiz Belardinelli、Ray A. Olsson

  DOI：10.1021/jm00043a010

  日期：1994.8

  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.
• 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：——
• New [<i>f</i>]-fused xanthines: Synthesis of 1,3-dipropyl-1<i>H</i>,3<i>H</i>-pyrazino, pyrido, pyrimido and pyrrolo[2, 1-<i>f</i>]purine-2,4-diones
  作者：Franco Gatta、Maria Rosaria Del Giudice、Anna Borioni、Carlo Mustazza

  DOI：10.1002/jhet.5570310115

  日期：1994.1

  Synthesis of 1,3-dipropyl-1H,3H-pyrazino, pyrido, pyrimido and pyrrolo[2,1-f]purine-2,4-diones, starting from 5,6-diamino-1,3-dipropylpyrimidine-2,4-dione 1 and 6-chloro-1,3-dipropylpyrimidine-2,4-dione 14 is described. A new synthetic approach to 1,3-dipropyl-1H,3H-pyrido(or pyrazino)[1′,2′-1,2]pyrimido[4,5-d]pyrimidine-2,4,5-triones 19 e, f, h has been also developed.

  从5,6-二氨基-1,3-二丙基嘧啶-开始，合成1,3-二丙基-1 H，3 H-吡嗪并，吡啶基，嘧啶基和吡咯并[2,1 - f ]嘌呤-2,4-二酮。描述了2，4-二酮1和6-氯-1，3-二丙基嘧啶-2，4-二酮14。1,3-二丙基-1 H，3 H-吡啶（或吡嗪并）[1'，2'-1,2]嘧啶[4,5 - d ]嘧啶-2,4,5-三酮的合成新方法还开发了19 e，f，h。