2-methylmorphanthridine-6,11(5H)-dione | 77047-17-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯氮卓类
• 英文名称: 2-methylmorphanthridine-6,11(5H)-dione
• 英文别名: 2-methyl-5H-dibenz[b,e]azepine-6,11-dione；2-Methyl-5H-dibenz[b,e]azepin-6,11-dion；2-Methyl-5H-dibenzo[b,e]azepine-6,11-dione；2-methyl-5H-benzo[c][1]benzazepine-6,11-dione
• CAS: 77047-17-7
• 化学式: C₁₅H₁₁NO₂
• 分子量: 237.258
• InChiKey: CCXGIDUIRMVHCR-UHFFFAOYSA-N

物化性质

• 熔点：
  238-240 °C
• 沸点：
  350.4±32.0 °C(Predicted)
• 密度：
  1.254±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  18
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  46.2
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-methylmorphanthridine-6,11(5H)-dione 在 sodium methylate 、 N,N-二甲基苯胺 、 三氯氧磷 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 8.0h， 生成 [6-Chloro-2-methyl-dibenzo[b,e]azepin-(11E)-ylidene]-acetonitrile
  参考文献：
  名称：

  Tricyclic epines. Novel (E)- and (Z)-11H-dibenz[b,e]azepines as potential central nervous system agents. Variation of the basic side chain

  摘要：

  The synthesis and pharmacological activity of new (E),(Z)-[6-(alkylamino)-11H-dibenz[b,e]azepin-11- ylidene]acetonitriles 12-45 and (E),(Z)-[6-(aminoalkoxy)-11H-dibenz[b,e]azepin-11-ylidene] acetonitriles 46-51 are described. The introduction of the cyanomethylene group into the 11-position of the 11H-dibenz[b,e]azepine framework has been carried out by a Wittig-Horner reaction under mild conditions. The (E),(Z) isomers were separated by fractional crystallization, assignment being achieved by X-ray analysis. A number of (E),(Z)-[6-(alkylamino)-11H-dibenz-[b,e]azepin-11-ylidene] acetonitriles (12, 14, 16, 20) show potent neuroleptic activity (2-7 times that of clozapine) in animal tests. The screening included tests for sedative and anticholinergic activity in mice, apomorphine and tryptamine antagonism in rats, and muscle-relaxing activity in rabbits. The divergence in the activity profile in the case of the separated (E),(Z) isomers has been observed as an interesting new aspect: the (Z) isomers show a significantly higher sedative and muscle-relaxant activity, whereas the (E) isomers possess a higher anticholinergic efficacy and somewhat greater apomorphine antagonism. Broad changes in the basic side chain were made in order to investigate structure-activity relationships. The important geometrical parameters for the molecules, obtained by X-ray analysis, were compared with the corresponding features in dopamine agonists and antagonists.

  DOI：

  10.1021/jm00160a015
• 作为产物：
  描述：

  N-(p-甲苯基)酞酰亚胺 在 三氯化铝 、 sodium chloride 作用下， 生成 2-methylmorphanthridine-6,11(5H)-dione
  参考文献：
  名称：

  DE551256

  摘要：

  公开号：

文献信息

• DE551256
  申请人：——

  公开号：——

  公开（公告）日：——
• STEINER G.; FRANKE A.; HADICKE E.; LENKE D.; TESCHENDORF H. -J.; HOFFMANN+, J. MED. CHEM., 29,(1986) N 10, 1877-1888
  作者：STEINER G.、 FRANKE A.、 HADICKE E.、 LENKE D.、 TESCHENDORF H. -J.、 HOFFMANN+

  DOI：——

  日期：——
• Tricyclic epines. Novel (E)- and (Z)-11H-dibenz[b,e]azepines as potential central nervous system agents. Variation of the basic side chain
  作者：Gerd Steiner、Albrecht Franke、Erich Haedicke、Dieter Lenke、Hans Juergen Teschendorf、Hans Peter Hofmann、Horst Kreiskott、Wolfgang Worstmann

  DOI：10.1021/jm00160a015

  日期：1986.10

  The synthesis and pharmacological activity of new (E),(Z)-[6-(alkylamino)-11H-dibenz[b,e]azepin-11- ylidene]acetonitriles 12-45 and (E),(Z)-[6-(aminoalkoxy)-11H-dibenz[b,e]azepin-11-ylidene] acetonitriles 46-51 are described. The introduction of the cyanomethylene group into the 11-position of the 11H-dibenz[b,e]azepine framework has been carried out by a Wittig-Horner reaction under mild conditions. The (E),(Z) isomers were separated by fractional crystallization, assignment being achieved by X-ray analysis. A number of (E),(Z)-[6-(alkylamino)-11H-dibenz-[b,e]azepin-11-ylidene] acetonitriles (12, 14, 16, 20) show potent neuroleptic activity (2-7 times that of clozapine) in animal tests. The screening included tests for sedative and anticholinergic activity in mice, apomorphine and tryptamine antagonism in rats, and muscle-relaxing activity in rabbits. The divergence in the activity profile in the case of the separated (E),(Z) isomers has been observed as an interesting new aspect: the (Z) isomers show a significantly higher sedative and muscle-relaxant activity, whereas the (E) isomers possess a higher anticholinergic efficacy and somewhat greater apomorphine antagonism. Broad changes in the basic side chain were made in order to investigate structure-activity relationships. The important geometrical parameters for the molecules, obtained by X-ray analysis, were compared with the corresponding features in dopamine agonists and antagonists.
• US2031143
  申请人：——

  公开号：——

  公开（公告）日：——