[3-(6-Methyl-5-thioxo-5,6,7,8-tetrahydro-9-oxa-1,6-diaza-benzocyclohepten-8-yl)-propyl]-carbamic acid tert-butyl ester | 104613-21-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: [3-(6-Methyl-5-thioxo-5,6,7,8-tetrahydro-9-oxa-1,6-diaza-benzocyclohepten-8-yl)-propyl]-carbamic acid tert-butyl ester
• CAS: 104613-21-0
• 化学式: C₁₇H₂₅N₃O₃S
• 分子量: 351.47
• InChiKey: HUIPEYBADFYEME-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.75
• 重原子数：
  24.0
• 可旋转键数：
  4.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  63.69
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  [3-(6-Methyl-5-thioxo-5,6,7,8-tetrahydro-9-oxa-1,6-diaza-benzocyclohepten-8-yl)-propyl]-carbamic acid tert-butyl ester 在 苯甲醚 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 生成 2-(3-aminopropyl)-2,3-dihydro-4-methylpyrido[3,2-f][1,4]oxazepine-5(4H)-thione
  参考文献：
  名称：

  Benzo- and pyrido-1,4-oxazepin-5-ones and -thiones: synthesis and structure-activity relationships of a new series of H1-antihistamines

  摘要：

  A series of novel benzo- and pyrido-1,4-oxazepinones and -thiones which represents a new structural class of compounds possessing H1 antihistaminic activity was synthesized, and the SARs were evaluated. The antihistaminic activity was determined by blockade of histamine-induced lethality in guinea pigs. The sedative potential was determined by comparison of the EEG profiles of the compounds with those of known sedating and nonsedating antihistamines. Several of the compounds were shown to possess potent H1 antihistaminic activity and to be free of the cortical slowing with synchronized waves and spindling activity found in the EEG of sedative antihistamines. One compound, 2-[2-(dimethylamino)ethyl]-3,4-dihydro-4-methylpyrido[3,2-f]-1,4- oxazepine-5(2H)-thione (rocastine) is currently undergoing clinical evaluation as a nonsedating H1 antihistamine.

  DOI：

  10.1021/jm00129a026
• 作为产物：
  描述：

  [3-(6-Methyl-5-oxo-5,6,7,8-tetrahydro-9-oxa-1,6-diaza-benzocyclohepten-8-yl)-propyl]-carbamic acid tert-butyl ester 在 劳森试剂 作用下， 以 甲苯 为溶剂， 反应 8.0h， 以42.6%的产率得到[3-(6-Methyl-5-thioxo-5,6,7,8-tetrahydro-9-oxa-1,6-diaza-benzocyclohepten-8-yl)-propyl]-carbamic acid tert-butyl ester
  参考文献：
  名称：

  Benzo- and pyrido-1,4-oxazepin-5-ones and -thiones: synthesis and structure-activity relationships of a new series of H1-antihistamines

  摘要：

  A series of novel benzo- and pyrido-1,4-oxazepinones and -thiones which represents a new structural class of compounds possessing H1 antihistaminic activity was synthesized, and the SARs were evaluated. The antihistaminic activity was determined by blockade of histamine-induced lethality in guinea pigs. The sedative potential was determined by comparison of the EEG profiles of the compounds with those of known sedating and nonsedating antihistamines. Several of the compounds were shown to possess potent H1 antihistaminic activity and to be free of the cortical slowing with synchronized waves and spindling activity found in the EEG of sedative antihistamines. One compound, 2-[2-(dimethylamino)ethyl]-3,4-dihydro-4-methylpyrido[3,2-f]-1,4- oxazepine-5(2H)-thione (rocastine) is currently undergoing clinical evaluation as a nonsedating H1 antihistamine.

  DOI：

  10.1021/jm00129a026