7-<2-(N-methyl-N-cyclohexyl)-aminoethyl>-1,3-dimethylxanthine

• 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: 7-<2-(N-methyl-N-cyclohexyl)-aminoethyl>-1,3-dimethylxanthine
• 英文别名: 7-[2-[Cyclohexyl(methyl)amino]ethyl]-1,3-dimethyl-purine-2,6-dione；7-[2-[cyclohexyl(methyl)amino]ethyl]-1,3-dimethylpurine-2,6-dione
• 化学式: C₁₆H₂₅N₅O₂
• 分子量: 319.407
• InChiKey: CABVCHSHFCSWNL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  61.7
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  茶碱 在 sodium hydroxide 作用下， 以 水 、 异丙醇 为溶剂， 反应 81.25h， 生成 7-<2-(N-methyl-N-cyclohexyl)-aminoethyl>-1,3-dimethylxanthine
  参考文献：
  名称：

  Synthesis, toxicological and pharmacological assessment of 7-substituted derivatives of 1,3-dimethylxanthine

  摘要：

  The synthesis of two 7-substituted theophylline derivatives from the theophylline sodium salt, dichloroalkane and N-methyl-N-cyclohexylamine is reported. The structures of the synthesized compounds were proved by microanalyses and H-1-NMR data. Acute toxicity studies of the compounds were performed on mice and rats. A comparative pharmacological study of the in vivo broncholytic effect of the derivatives and aminophylline showed that the new compounds have different bronchodilatory activity and the compound 7-[2-(N-methyl-N-cyclohexyl)-aminoethyl] 1,3-dimethylxanthine tartrate 3a was more active than 7-[3-(N-methyl-N-cyclohexyl)-aminopropyl]-1,3-dimethylxanthine hydrochloride 3b. It was demonstrated that compound 3b and aminophylline exerted the strongest inhibitory effect on the enzyme activity of phosphodiesterase in lung homogenate. Compound 3a showed a slight inhibitory effect on the enzyme activity in this homogenate. The possible mechanisms of the broncholytic effects of these compounds are discussed.

  DOI：

  10.1016/0223-5234(94)90099-x

文献信息

• Synthesis, toxicological and pharmacological assessment of 7-substituted derivatives of 1,3-dimethylxanthine
  作者：PT Peikov、AB Zlatkov、MT Markov、ND Danchev、DI Ivanov、JT Panova

  DOI：10.1016/0223-5234(94)90099-x

  日期：1994.1

  The synthesis of two 7-substituted theophylline derivatives from the theophylline sodium salt, dichloroalkane and N-methyl-N-cyclohexylamine is reported. The structures of the synthesized compounds were proved by microanalyses and H-1-NMR data. Acute toxicity studies of the compounds were performed on mice and rats. A comparative pharmacological study of the in vivo broncholytic effect of the derivatives and aminophylline showed that the new compounds have different bronchodilatory activity and the compound 7-[2-(N-methyl-N-cyclohexyl)-aminoethyl] 1,3-dimethylxanthine tartrate 3a was more active than 7-[3-(N-methyl-N-cyclohexyl)-aminopropyl]-1,3-dimethylxanthine hydrochloride 3b. It was demonstrated that compound 3b and aminophylline exerted the strongest inhibitory effect on the enzyme activity of phosphodiesterase in lung homogenate. Compound 3a showed a slight inhibitory effect on the enzyme activity in this homogenate. The possible mechanisms of the broncholytic effects of these compounds are discussed.