2-[2-(Dimethylamino)ethyl]-7-methoxy-4-methyl-2,3-dihydro-1,4-benzoxazepine-5-thione | 121675-08-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并恶嗪类
• 英文名称: 2-[2-(Dimethylamino)ethyl]-7-methoxy-4-methyl-2,3-dihydro-1,4-benzoxazepine-5-thione
• CAS: 121675-08-9
• 化学式: C₁₅H₂₂N₂O₂S
• 分子量: 294.418
• InChiKey: CGEFIKSTXLWLDM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  57
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  3-羟基-1-甲基四氢吡咯 在 sodium hydroxide 、 氯化亚砜 、 tetraphosphorus decasulfide 、 potassium sulfide 、 sodium hydride 、 三乙胺 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 、 甲苯 、 苯 为溶剂， 反应 0.75h， 生成 2-[2-(Dimethylamino)ethyl]-7-methoxy-4-methyl-2,3-dihydro-1,4-benzoxazepine-5-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

文献信息

• Benzo- and pyrido-1,4-oxazepin-5-ones and -thiones: synthesis and structure-activity relationships of a new series of H1-antihistamines
  作者：Albert D. Cale、Thomas W. Gero、Kathleen R. Walker、Young S. Lo、William J. Welstead、Larry W. Jaques、Ashby F. Johnson、Charles A. Leonard、Joseph C. Nolan、David N. Johnson

  DOI：10.1021/jm00129a026

  日期：1989.9

  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.