1,3,6,7-tetrahydro-(8H)-imidazo[2,1-f]theophylline | 49687-12-9

• 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: 1,3,6,7-tetrahydro-(8H)-imidazo[2,1-f]theophylline
• 英文别名: 1,3-dimethyl-7,8-dihydro-1H,6H-imidazo[2,1-f]purine-2,4-dione；1,3-dimethyl-7,8-dihydro-1H-imidazo[2,1-f]purine-2,4(3H,6H)-dione；2,4-dimethyl-7,8-dihydro-6H-purino[7,8-a]imidazole-1,3-dione
• CAS: 49687-12-9
• 化学式: C₉H₁₁N₅O₂
• mdl: MFCD03423805
• 分子量: 221.219
• InChiKey: IRBZSBWYQZJUJQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.4
• 重原子数：
  16
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.444
• 拓扑面积：
  70.5
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  7-(2-bromoethyl)-8-bromotheophylline 在 氨 作用下， 以 乙醇 为溶剂， 反应 5.0h， 以60%的产率得到1,3,6,7-tetrahydro-(8H)-imidazo[2,1-f]theophylline
  参考文献：
  名称：

  Synthesis and CNS activity of tricyclic theophylline derivatives. 8-substituted imidazo[2,1-f]theophyllines

  摘要：

  Based on previously described results of pharmacological in vitro and in vivo tests of some series of pyrimido- and diazepino-[2,1-f]theophylline derivatives, Ns-unsubstituted, N8-benzyl and N8-arylpiperazino-alkyl derivatives of imidazo[2,1-f]theophyllines were synthesized and tested for their CNS activity. It has been shown that tricyclic [2,1-f]theophyllines possess sedative and analgesic activity. N8-Phenylpiperazinopropyl-1,3,6,7-tetrahydro-(8H)-imidazo[2,1-f]theophylline 6 showed significant anti-serotonin and long-lasting hypothermic effects. N8-Benzyl-1,3,6,8-tetrahydroimidazo-7-on[2,1-f]theophylline 8 possess anticonvulsant properties. (C) 1999 Editions scientifiques et medicales Elsevier SAS.

  DOI：

  10.1016/s0223-5234(99)00131-2

文献信息

• Facile synthesis of fused purines from 8-aminotheophylline
  作者：Taisei Ueda、Rikisei Oh、Shin-Ichi Nagai、Jinsaku Sakakibara

  DOI：10.1002/jhet.5570350125

  日期：1998.1

  Fused purines 3a-f were prepared by one-step from 8-aminotheophylline (1) and α,ω-dibromoalkanes in N, N-dimethylformamide in the presence of sodium hydride. Reaction of 3c-e with chloroacetyl chloride followed by treatment with dimethylamine gave 6a-c. A one-step reaction of 1 with ethyl bromopropionate gave 1,3-dimethyl-1,2,3,4,6,7,8,9-octahydropyrimido[2,1-f]purine-2,4,8-trione (7b). Facile syntheses

  在氢化钠存在下，由N - N-二甲基甲酰胺中的8-氨基茶碱（1）和α，ω-二溴代烷烃一步一步制备融合的嘌呤3a-f。的反应3C-E与氯乙酰氯，接着用二甲胺，得到6A-C 。1与溴丙酸乙酯的一步反应，得到1,3-二甲基-1,2,3,4,6,7,8,9-八氢嘧啶[ 2,1- f ]嘌呤-2,4,8-三酮（7b）。还可以轻松地从1合成7a，c，d。