Basic derivatives of 6,7-dihydroindolo[1,7-ab][1]benzazepine and 6H-indolo[7,1-cd][1,5]benzoxazepine as potential antidepressant agents

Basic derivatives of 6,7-dihydroindolo[1,7-ab][1]benzazepine and 6H-indolo[7,1-cd][1,5]benzoxazepine incorporating the imipramine basic side chain were synthesized and screened for antidepressant activity in mice. With few exceptions, the compounds unsubstituted at C-2 antagonized reserpine-induced...

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Bibliographic Details
Published in:Journal of medicinal chemistry 1976-02, Vol.19 (2), p.208-213
Main Authors: Toscano, Luciano, Grisanti, Giampiero, Fioriello, Giuseppe, Seghetti, Ennio, Bianchetti, Alberto, Bossoni, Giuseppe, Riva, Mario
Format: Article
Language:English
Subjects:
Animals
Antidepressive Agents - chemical synthesis
Antidepressive Agents - pharmacology
Antidepressive Agents - toxicity
Benzazepines - chemical synthesis
Benzazepines - pharmacology
Benzazepines - toxicity
Blepharoptosis - prevention & control
Body Temperature - drug effects
Depression, Chemical
Guinea Pigs
Ileum - drug effects
In Vitro Techniques
Indoles - chemical synthesis
Indoles - pharmacology
Indoles - toxicity
Lethal Dose 50
Male
Mice
Muscle Contraction - drug effects
Muscle, Smooth - drug effects
Reserpine - antagonists & inhibitors
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Summary:Basic derivatives of 6,7-dihydroindolo[1,7-ab][1]benzazepine and 6H-indolo[7,1-cd][1,5]benzoxazepine incorporating the imipramine basic side chain were synthesized and screened for antidepressant activity in mice. With few exceptions, the compounds unsubstituted at C-2 antagonized reserpine-induced ptosis and hypothermia showing negligible anticholinergic and antihistaminic properties. The compound 1-[2-(N-methyl-N-benzylamino)ethyl]-6,7-dihydroindolo[1,7-ab][1]benzazepine had the highest toxicity-activity ratio.
ISSN:0022-2623
1520-4804
DOI:10.1021/jm00224a003