3,7-dihydro-1,3-dimethyl-7-<3-<4-<3-(phenylthio)propyl>piperazin-1-yl>propyl>-1H-purine-2,6-dione | 79730-42-0

• 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: 3,7-dihydro-1,3-dimethyl-7-<3-<4-<3-(phenylthio)propyl>piperazin-1-yl>propyl>-1H-purine-2,6-dione
• 英文别名: 3,7-dihydro-1,3-dimethyl-7-(3-{4-[3-(phenylthio)propyl]piperazin-1-yl}propyl)-1H-purine-2,6-dione；7-[3-[4-(3-Phenylthio-propyl)-1-piperazinyl]-propyl]-theophylline；1,3-dimethyl-7-[3-[4-(3-phenylsulfanylpropyl)piperazin-1-yl]propyl]purine-2,6-dione
• CAS: 79730-42-0
• 化学式: C₂₃H₃₂N₆O₂S
• 分子量: 456.612
• InChiKey: XFZVKWUIDLNCKJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  32
• 可旋转键数：
  9
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  90.2
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  3-氯丙基苯基硫醚 在 sodium hydroxide 、 potassium carbonate 作用下， 以 乙醇 为溶剂， 反应 48.0h， 生成 3,7-dihydro-1,3-dimethyl-7-<3-<4-<3-(phenylthio)propyl>piperazin-1-yl>propyl>-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

文献信息

• Piperazine derivatives of theophylline
  申请人：LAROCHE NAVARRON S.A. Société dite:

  公开号：EP0033674B1

  公开（公告）日：1984-08-15
• US4374835A
  申请人：——

  公开号：US4374835A

  公开（公告）日：1983-02-22
• New Antihistaminic Theophylline or Theobromine Derivatives
  作者：Jean-Claude Pascal、Serge Beranger、Henri Pinhas、Alain Poizot、Jean-Pierre Désiles

  DOI：10.1021/jm50001a019

  日期：1985.5

  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.