3,7-dihydro-3,7-dimethyl-1-<3-<4-<3-(phenylthio)propyl>piperazin-1-yl>-2-hydroxypropyl>-1H-purine-2,6-dione | 86590-99-0

• 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-3,7-dimethyl-1-<3-<4-<3-(phenylthio)propyl>piperazin-1-yl>-2-hydroxypropyl>-1H-purine-2,6-dione
• 英文别名: 1-(3-theobromin-1-yl-2-hydroxypropyl)-4-(3-phenyl-thiopropyl)piperazine；1-(3-Theobromin-1-yl-2-hydroxypropyl)-4-(3-phenylthiopropyl)piperazine；1-[2-hydroxy-3-[4-(3-phenylsulfanylpropyl)piperazin-1-yl]propyl]-3,7-dimethylpurine-2,6-dione
• CAS: 86590-99-0
• 化学式: C₂₃H₃₂N₆O₃S
• 分子量: 472.611
• InChiKey: FGACXCBYUROJBZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  33
• 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：
  110
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  3-氯丙基苯基硫醚 在 sodium hydroxide 作用下， 以 乙醇 为溶剂， 反应 48.0h， 生成 3,7-dihydro-3,7-dimethyl-1-<3-<4-<3-(phenylthio)propyl>piperazin-1-yl>-2-hydroxypropyl>-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 theobromine
  申请人：Laroche Navarron, S.A.

  公开号：US04374837A1

  公开（公告）日：1983-02-22

  New compounds of the formula ##STR1## and the pharmaceutically acceptable acid addition salts thereof, wherein Z.sub.1 and Z.sub.2 are each independently selected from the group consisting of CH.sub.2, CHOB and C.dbd.O, wherein B is selected from the group consisting of hydrogen and alkanoyl; Y is oxygen or sulfur; n is an integer from 0-4 but cannot be zero when Z.sub.1 is CHOB; m is an integer from 0-4 but cannot be zero when Z.sub.2 is CHOB; and R.sub.1, R.sub.2 and R.sub.3 are each independently hydrogen, halogen, hydroxy, trifluoromethyl, alkyl or alkoxy; are antihistamines and are therefore useful in the treatment of respiratory diseases including asthma, hay fever, allergies and the common cold.

  新的化合物公式为##STR1##及其药用酸盐，其中Z.sub.1和Z.sub.2各自独立地选自CH.sub.2，CHOB和C.dbd.O组成的群体，其中B选自氢和烷酰基；Y为氧或硫；n为0-4的整数，但当Z.sub.1为CHOB时不能为零；m为0-4的整数，但当Z.sub.2为CHOB时不能为零；R.sub.1，R.sub.2和R.sub.3各自独立地为氢，卤素，羟基，三氟甲基，烷基或烷氧基；是抗组胺药物，因此在治疗呼吸道疾病包括哮喘，花粉症，过敏和普通感冒中有用。
• FAVIER, C.;PINHAS, H.;BERANGER, S.;PASCAL, J. -C.
  作者：FAVIER, C.、PINHAS, H.、BERANGER, S.、PASCAL, J. -C.

  DOI：——

  日期：——
• US4374837A
  申请人：——

  公开号：US4374837A

  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.