3-methyl-6,11-dioxo-5,6-dihydro-morphanthridine | 1218-70-8

• 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: 3-methyl-6,11-dioxo-5,6-dihydro-morphanthridine
• 英文别名: 3-methylmorphanthridine-6,11(5H)-dione；3-Methyl-morphanthridin-6,11-dion；3-methyl-5H-dibenzo[b,e]azepine-6,11-dione；3-methyl-5H-dibenz[b,e]azepine-6,11-dione；3-Methyl-5H-dibenz[b,e]azepin-6,11-dion；3-Methyl-5H-dibenz[b,e]azepine-6,11-dione；3-methyl-5H-benzo[c][1]benzazepine-6,11-dione
• CAS: 1218-70-8
• 化学式: C₁₅H₁₁NO₂
• 分子量: 237.258
• InChiKey: KLFUBDBUZWAKNZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 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：

  3-methyl-6,11-dioxo-5,6-dihydro-morphanthridine 在 氯化亚砜 、 盐酸羟胺 作用下， 以 吡啶 、 乙醚 、 乙醇 为溶剂， 反应 0.83h， 生成 2-methyldibenzo<1,4>diazocine-6,11-dione
  参考文献：
  名称：

  大环化合物的研究：一些新的吗啡啉和重氮辛的合成

  摘要：

  摘要 已开发出一种合成 2 或 3-取代的 5,6-二氢-6,11-二氧代-morphanthridines (2) 的新方法，该方法涉及苯胺酸 (1) 与 PPA/AcOH 的环化。一种新的杂环系统，2 或 3-取代 5,6,11,12-四氢二苯并[b, f] [1,4]diazocine-6,11-diones (4) 已以优异的产率合成。

  DOI：

  10.1081/scc-120004842
• 作为产物：
  描述：

  N-乙酰基-3-甲苯胺 在 盐酸 、 三氯化铝 、 水 、 1,1,2,2-四氯乙烷 作用下， 生成 3-methyl-6,11-dioxo-5,6-dihydro-morphanthridine
  参考文献：
  名称：

  Kraenzlein, Chemische Berichte, 1937, vol. 70, p. 1952,1961

  摘要：

  DOI：

文献信息

• 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.
• 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：——
• Kraenzlein, Chemische Berichte, 1937, vol. 70, p. 1952,1961
  作者：Kraenzlein

  DOI：——

  日期：——
• STUDIES IN LARGE RING COMPOUNDS: SYNTHESIS OF SOME NEW MORPHANTHRINDINES AND DIAZOCINES
  作者：V. G. Pawar、S. R. Bhusare、R. P. Pawar、B. M. Bhawal

  DOI：10.1081/scc-120004842

  日期：2002.1

  ABSTRACT A novel method for the synthesis of 2 or 3-substituted 5,6-dihydro-6,11-dioxo-morphanthridines (2) involving the cyclisation of anilinic acid (1) with PPA/AcOH has been developed. A new heterocyclic system, 2 or 3-Substituted 5,6,11,12-tetrahydrodibenzo[b, f] [1,4]diazocine-6,11-diones (4) has been synthesized with excellent yields.

  摘要 已开发出一种合成 2 或 3-取代的 5,6-二氢-6,11-二氧代-morphanthridines (2) 的新方法，该方法涉及苯胺酸 (1) 与 PPA/AcOH 的环化。一种新的杂环系统，2 或 3-取代 5,6,11,12-四氢二苯并[b, f] [1,4]diazocine-6,11-diones (4) 已以优异的产率合成。