9-acetyl-1,2,3,9-tetrahydro-3-[(2-methyl-1H-imidazol-1-yl)methyl]-4H-carbazol-4-one

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: 9-acetyl-1,2,3,9-tetrahydro-3-[(2-methyl-1H-imidazol-1-yl)methyl]-4H-carbazol-4-one
• 英文别名: 9-acetyl-3-[(2-methylimidazol-1-yl)methyl]-2,3-dihydro-1H-carbazol-4-one
• 化学式: C₁₉H₁₉N₃O₂
• 分子量: 321.379
• InChiKey: BNIGVWWZUROBAL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  24
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  56.9
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  乙酰氯 、 1,2,3,9-四氢-3-[(2-甲基-1H-咪唑-1-基)甲基]-4H-咔唑-4-酮 以 N-甲基乙酰胺 、 mineral oil 为溶剂， 生成 9-acetyl-1,2,3,9-tetrahydro-3-[(2-methyl-1H-imidazol-1-yl)methyl]-4H-carbazol-4-one
  参考文献：
  名称：

  Carbazole derivatives and their use as 5HT-induced antagonists

  摘要：

  本发明涉及通式（I）的化合物：其中R.sup.1代表CO.sub.2 R.sup.5、COR.sup.5、CONR.sup.5 R.sup.6或SO.sub.2 R.sup.5（其中R.sup.5和R.sup.6，可以相同也可以不同，分别代表氢原子、C.sub.1-6烷基或C.sub.3-7环烷基，或苯基或苯基-(C.sub.1-4)烷基，其中苯基可能通过一个或多个C.sub.1-4烷基、C.sub.1-4烷氧基或羟基或卤素原子取代，但R.sup.5不代表氢原子时，R.sup.1代表CO.sub.2 R.sup.5或SO.sub.2 R.sup.5的群）；以及由R.sup.2、R.sup.3和R.sup.4代表的群中的一个是氢原子或C.sub.1-6烷基、C.sub.3-7环烷基、C.sub.2-6烯丙基或苯基-(C.sub.1-3)烷基，另外两个群中的每一个，可以相同也可以不同，代表氢原子或C.sub.1-6烷基群；以及其生理上可接受的盐和溶剂化物。这些化合物是"神经元"5-羟色胺受体的有效和选择性拮抗剂，可用于治疗精神分裂症（如精神分裂症和狂躁症）；焦虑；疼痛；胃瘫；胃肠功能障碍的症状，如消化不良、消化性溃疡、反流性食管炎和胀气；偏头痛；以及恶心和呕吐。

  公开号：

  US04749718A1

文献信息

• Substituted imidazolylmethyltetrahydro-carbazolones
  申请人：GLAXO GROUP LIMITED

  公开号：EP0210840A2

  公开（公告）日：1987-02-04

  The invention relates to compounds of the general formula (I): wherein R' represents a group CO2R5, COR5, CONR5R6 or SO2R5 (wherein R5 and R6, which may be the same or different, each represents a hydrogen atom, a C1-6 alkyl or C3.7 cycloalkyl group, or a phenyl or phenyl- (C1-4) alkyl group in which the phenyl group is optionally substituted by one or more C1-4 alkyl, C1-4, alkoxy or hydroxy groups or halogen atoms, with the proviso that R5 does not represent a hydrogen atom when R' represents a group CO2R5 or SO2R5); and one of the groups represented by R2, R3 and R4 is a hydrogen atom or a C1-6 alkyl, C3-7 cycloalkyl, C2-6 alkenyl or phenyl-(C1-3)alkyl group and each of the other two groups, which may be the same or different, represents a hydrogen atom or a C1-6 alkyl group; and physiologically acceptable salts and solvates thereof. The compounds are potent and selective antagonists of "neuronal" 5-hydroxytryptamine receptors and are useful in the treatment of psychotic disorders (e.g. schizophrenia and mania); anxiety; pain; gastric stasis; symptoms of gastrointestinal dysfunction such as occur with dyspepsia, peptic ulcer, reflux oesophagitis and flatulence; migraine; and nausea and vomiting.

  本发明涉及通式 (I) 的化合物： 其中 R'代表基团 CO2R5、COR5、CONR5R6 或 SO2R5（其中 R5 和 R6 可以相同或不同，各自代表氢原子、C1-6 烷基或 C3.7环烷基，或苯基或苯基-(C1-4)烷基，其中苯基任选被一个或多个C1-4烷基、C1-4、烷氧基或羟基或卤素原子取代，但当R'代表CO2R5或SO2R5基团时，R5不代表氢原子）；R2、R3 和 R4 所代表的基团之一是氢原子或 C1-6 烷基、C3-7 环烷基、C2-6 烯基或苯基-(C1-3)烷基，而另外两个基团（可以相同或不同）分别代表氢原子或 C1-6 烷基；及其生理上可接受的盐和溶剂。 这些化合物是 "神经元 "5-羟色胺受体的强效选择性拮抗剂，可用于治疗精神病（如精神分裂症和躁狂症）、焦虑、疼痛、胃淤血、胃肠功能紊乱症状（如消化不良、消化性溃疡、反流性食管炎和胀气）、偏头痛以及恶心和呕吐。
• US4749718A
  申请人：——

  公开号：US4749718A

  公开（公告）日：1988-06-07
• Carbazole derivatives and their use as 5HT-induced antagonists
  申请人：Glaxo Group Limited

  公开号：US04749718A1

  公开（公告）日：1988-06-07

  The invention relates to compounds of the general formula (I): ##STR1## wherein R.sup.1 represents a group CO.sub.2 R.sup.5, COR.sup.5, CONR.sup.5 R.sup.6 or SO.sub.2 R.sup.5 (wherein R.sup.5 and R.sup.6, which may be the same or different, each represents a hydrogen atom, a C.sub.1-6 alkyl or C.sub.3-7 cycloalkyl group, or a phenyl or phenyl-(C.sub.1-4)alkyl group in which the phenyl group is optionally substituted by one or more C.sub.1-4 alkyl, C.sub.1-4 alkoxy or hydroxy groups or halogen atoms, with the proviso that R.sup.5 does not represent a hydrogen atom when R.sup.1 represents a group CO.sub.2 R.sup.5 or SO.sub.2 R.sup.5); and one of the groups represented by R.sup.2, R.sup.3 and R.sup.4 is a hydrogen atom or a C.sub.1-6 alkyl, C.sub.3-7 cycloalkyl, C.sub.2-6 alkenyl or phenyl-(C.sub.1-3)alkyl group and each of the other two groups, which may be the same or different, represents a hydrogen atom or a C.sub.1-6 alkyl group; and physiologically acceptable salts and solvates thereof. The compounds are potent and selective antagonists of "neuronal" 5-hydroxytryptamine receptors and are useful in the treatment of psychotic disorders (e.g. schizophrenia and mania); anxiety; pain; gastric stasis; symptoms of gastrointestinal dysfunction such as occur with dyspepsia, peptic ulcer, reflux oesophagitis and flatulence; migraine; and nausea and vomiting.

  本发明涉及通式（I）的化合物：其中R.sup.1代表CO.sub.2 R.sup.5、COR.sup.5、CONR.sup.5 R.sup.6或SO.sub.2 R.sup.5（其中R.sup.5和R.sup.6，可以相同也可以不同，分别代表氢原子、C.sub.1-6烷基或C.sub.3-7环烷基，或苯基或苯基-(C.sub.1-4)烷基，其中苯基可能通过一个或多个C.sub.1-4烷基、C.sub.1-4烷氧基或羟基或卤素原子取代，但R.sup.5不代表氢原子时，R.sup.1代表CO.sub.2 R.sup.5或SO.sub.2 R.sup.5的群）；以及由R.sup.2、R.sup.3和R.sup.4代表的群中的一个是氢原子或C.sub.1-6烷基、C.sub.3-7环烷基、C.sub.2-6烯丙基或苯基-(C.sub.1-3)烷基，另外两个群中的每一个，可以相同也可以不同，代表氢原子或C.sub.1-6烷基群；以及其生理上可接受的盐和溶剂化物。这些化合物是"神经元"5-羟色胺受体的有效和选择性拮抗剂，可用于治疗精神分裂症（如精神分裂症和狂躁症）；焦虑；疼痛；胃瘫；胃肠功能障碍的症状，如消化不良、消化性溃疡、反流性食管炎和胀气；偏头痛；以及恶心和呕吐。