(E)-7-(4-chloro-2-buten-1-yl)theophylline | 95250-76-3

• 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: (E)-7-(4-chloro-2-buten-1-yl)theophylline
• CAS: 95250-76-3
• 化学式: C₁₁H₁₃ClN₄O₂
• 分子量: 268.703
• InChiKey: VNUAYVRLXKZDPO-ONEGZZNKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.23
• 重原子数：
  18.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  61.82
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  (E)-7-(4-chloro-2-buten-1-yl)theophylline 、 N(3-苯基硫代-1-丙基)哌嗪 在 potassium carbonate 作用下， 以 乙醇 为溶剂， 反应 24.0h， 生成 3,7-dihydro-1,3-dimethyl-7-<4-<4-<3-(phenylthio)propyl>piperazin-1-yl>-2-butenyl>-1H-purine-2,6-dione
  参考文献：
  名称：

  New Antihistaminic Theophylline or Theobromine Derivatives

  摘要：

  A series of 3,4-dihydro-1,3-dimethyl-7-[3-(4-substituted-piperazin-1-yl)- substituted-alkyl]-1H-purine-2,6-diones and 3,7-dihydro-3,7-dimethyl-1-[3-(4-substituted-piperazin-1-yl)- substituted-alkyl]-1H-purine-2,6-diones was synthesized and evaluated for antihistaminic activity. Some of them displayed good inhibition of both histamine-induced bronchospasm in the anesthetized guinea pig at 10 micrograms/kg by the intravenous route and of passive cutaneous anaphylaxis in the rat at 10 mg/kg by the oral route. Comparison of the two most active compounds revealed a higher antihistaminic activity with the compounds containing a (phenylthio)propyl group (1 and 2) as compared with that containing a phenoxy group. Compound 2 [RS-49014, 3,4-dihydro-1,3-dimethyl-7-[3-[4-[3-(phenylthio)propyl]piperazin-1 -yl]- 2-hydroxypropyl]-1H-purine-2,6-dione] was selected for clinical trials on the basis of a comparative pharmacological study with chlorpheniramine, ketotifen, promethazine, and theophylline.

  DOI：

  10.1021/jm50001a019
• 作为产物：
  描述：

  反式-1,4-二氯-2-丁烯 、 1,3-Dimethylxanthine potassium salt 以70%的产率得到(E)-7-(4-chloro-2-buten-1-yl)theophylline
  参考文献：
  名称：

  New Antihistaminic Theophylline or Theobromine Derivatives

  摘要：

  A series of 3,4-dihydro-1,3-dimethyl-7-[3-(4-substituted-piperazin-1-yl)- substituted-alkyl]-1H-purine-2,6-diones and 3,7-dihydro-3,7-dimethyl-1-[3-(4-substituted-piperazin-1-yl)- substituted-alkyl]-1H-purine-2,6-diones was synthesized and evaluated for antihistaminic activity. Some of them displayed good inhibition of both histamine-induced bronchospasm in the anesthetized guinea pig at 10 micrograms/kg by the intravenous route and of passive cutaneous anaphylaxis in the rat at 10 mg/kg by the oral route. Comparison of the two most active compounds revealed a higher antihistaminic activity with the compounds containing a (phenylthio)propyl group (1 and 2) as compared with that containing a phenoxy group. Compound 2 [RS-49014, 3,4-dihydro-1,3-dimethyl-7-[3-[4-[3-(phenylthio)propyl]piperazin-1 -yl]- 2-hydroxypropyl]-1H-purine-2,6-dione] was selected for clinical trials on the basis of a comparative pharmacological study with chlorpheniramine, ketotifen, promethazine, and theophylline.

  DOI：

  10.1021/jm50001a019