2-chloro-N-<3-(dimethylamino)-2-hydroxypropyl>-N-methylbenzamide | 121675-22-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 2-chloro-N-<3-(dimethylamino)-2-hydroxypropyl>-N-methylbenzamide
• 英文别名: 2-chloro-N-[3-(dimethylamino)-2-hydroxypropyl]-N-methylpyridine-3-carboxamide
• CAS: 121675-22-7
• 化学式: C₁₂H₁₈ClN₃O₂
• 分子量: 271.747
• InChiKey: REYBLEVFJVLVLY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  56.7
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-chloro-N-<3-(dimethylamino)-2-hydroxypropyl>-N-methylbenzamide 在 sodium hydride 作用下， 以 甲苯 、 paraffin 为溶剂， 反应 0.33h， 以8.8 g的产率得到2-(Dimethylamino)methyl-2,3-dihydro-4-methylpyrido[3,2-f][1,4]-oxazepin-5(4H)-one
  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：

  2-氯烟酸 、 1-(dimethylamino)-3-(methylamino)-2-propanol hydrochloride 在 N,N'-二环己基碳二亚胺 作用下， 以 水 、 乙腈 为溶剂， 以26.97 g的产率得到2-chloro-N-<3-(dimethylamino)-2-hydroxypropyl>-N-methylbenzamide
  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

• Process for the preparation of aromatic-1,4-oxazepinones and thiones
  申请人：A.H. ROBINS COMPANY, INCORPORATED (a Delaware corporation)

  公开号：EP0175570A2

  公开（公告）日：1986-03-26

  1,4-Oxazepinones and thiones of general formula b where aromatic ring selected from benzene, naphtha- pyridine; n is 1 to 3; Z is an amino radicar; , cycloalkyl or phenyl-loweratkvl; and R4 and R6 are hydrogen and loweralkyl, may be prepared by of general formula II or general formula which in turn may be prepared from chloroaromatic carboxylates and alkanolamines.

  通式 b 的 1,4-氧氮杂卓酮和硫酮 其中芳香环选自苯、石脑油-吡啶；n 为 1 至 3；Z 为氨基辐射体；、环烷基或苯基-低级烷基；R4 和 R6 为氢和低级烷基，可通过通式 II 或通式制备 它们又可由氯芳羧酸酯和烷醇胺制备。
• ——
  作者：LO YOUNG S.、 CALE , JR.、 ALBERT D.

  DOI：——

  日期：——
• US4610819A
  申请人：——

  公开号：US4610819A

  公开（公告）日：1986-09-09
• US4783535A
  申请人：——

  公开号：US4783535A

  公开（公告）日：1988-11-08
• 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.