2,4-dimethyl-1,3-dioxo-7,8-dihydro-5H-purino[7,8-a]imidazole-7-carboxylic acid

• 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: 2,4-dimethyl-1,3-dioxo-7,8-dihydro-5H-purino[7,8-a]imidazole-7-carboxylic acid
• 化学式: C₁₀H₁₁N₅O₄
• 分子量: 265.228
• InChiKey: DIJMJMFKTZVOGK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.8
• 重原子数：
  19
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  108
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  1-(3-氨基)-4-(2-甲氧基苯基)哌嗪 、 2,4-dimethyl-1,3-dioxo-7,8-dihydro-5H-purino[7,8-a]imidazole-7-carboxylic acid 在 1-羟基苯并三唑 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 12.5h， 以51%的产率得到1,3-dimethyl-6,7-dihydroimidazo[2,1-f]purine-2,4-(1H,3H)-dione-7-carboxylic acid n-2-[N4-(2-methoxy)-phenyl-piperazin-N1-yl]-ethyl amide
  参考文献：
  名称：

  Synthesis and preliminary pharmacological evaluation of imidazo[2,1-f]purine-2,4-dione derivatives

  摘要：

  A series of N-8-arylpiperazinylpropyl derivatives of 1,3-dimethyl-(1H,8H)-imidazo[2,1-f]purine-2,4-dione (2-10) and amide derivatives of 1,3-dimethyl-6,7-dihydroimidazo[2,1-f]purine-2,4-(1H,3H)-dione-7-carboxylic acid (11-13) were synthesized. Compounds (2-10) evaluated in vitro were potent 5-HT1A receptor ligands. Preclinical studies indicated that 8-[3-(N4-phenyl)-piperazin-N1-yl-propyl]-1,3-dimethyl(1H,8H)-imidazo[2,1-f]purine-2,4-dione (2) exerts anxiolytic-like activity in the four-plate test in mice: however its effect was weaker, than that produced by Diazepam. This compound and 8-[3-(N4-2'-metoxyphenyl)-piperazin-N1-yl-propyl]-1,3-dimethyl-(1H,8H)-imidazo[2,1-f]purine-2,4-dione (3) behaved like antidepressants in the forced swimming test in mice; and their activity in that model was comparable with the effect of Imipramine. The obtained results suggested that the long-chain arylpiperazines (LCAPs) linked to tricyclic derivatives of the theophylline remain a worthy of future research for obtaining new derivatives with potential anxiolytic/antidepressant activity. (C) 2009 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2009.07.014
• 作为产物：
  描述：

  8-benzyl-6,7-dihydro-[8H]-imidazo[2,1-f]theophylline-7-carboxylic acid ethyl ester 在 硫酸 、 sodium ethanolate 作用下， 以 乙醇 为溶剂， 反应 0.25h， 生成 2,4-dimethyl-1,3-dioxo-7,8-dihydro-5H-purino[7,8-a]imidazole-7-carboxylic acid
  参考文献：
  名称：

  Pawlowski; Katlabi; Rys, Pharmazie, 1997, vol. 52, # 4, p. 279 - 282

  摘要：

  DOI：

文献信息

• Synthesis and preliminary pharmacological evaluation of imidazo[2,1-f]purine-2,4-dione derivatives
  作者：Agnieszka Zagórska、Sławomir Jurczyk、Maciej Pawłowski、Małgorzata Dybała、Gabriel Nowak、Ewa Tatarczyńska、Agnieszka Nikiforuk、Ewa Chojnacka-Wójcik

  DOI：10.1016/j.ejmech.2009.07.014

  日期：2009.11

  A series of N-8-arylpiperazinylpropyl derivatives of 1,3-dimethyl-(1H,8H)-imidazo[2,1-f]purine-2,4-dione (2-10) and amide derivatives of 1,3-dimethyl-6,7-dihydroimidazo[2,1-f]purine-2,4-(1H,3H)-dione-7-carboxylic acid (11-13) were synthesized. Compounds (2-10) evaluated in vitro were potent 5-HT1A receptor ligands. Preclinical studies indicated that 8-[3-(N4-phenyl)-piperazin-N1-yl-propyl]-1,3-dimethyl(1H,8H)-imidazo[2,1-f]purine-2,4-dione (2) exerts anxiolytic-like activity in the four-plate test in mice: however its effect was weaker, than that produced by Diazepam. This compound and 8-[3-(N4-2'-metoxyphenyl)-piperazin-N1-yl-propyl]-1,3-dimethyl-(1H,8H)-imidazo[2,1-f]purine-2,4-dione (3) behaved like antidepressants in the forced swimming test in mice; and their activity in that model was comparable with the effect of Imipramine. The obtained results suggested that the long-chain arylpiperazines (LCAPs) linked to tricyclic derivatives of the theophylline remain a worthy of future research for obtaining new derivatives with potential anxiolytic/antidepressant activity. (C) 2009 Elsevier Masson SAS. All rights reserved.
• Pawlowski; Katlabi; Rys, Pharmazie, 1997, vol. 52, # 4, p. 279 - 282
  作者：Pawlowski、Katlabi、Rys、Szneler

  DOI：——

  日期：——