Abstract
The synthesis of the tetracyclic compounds 1-(4,5-dichloro-9,10-dihydro-9,10-ethanoanthracen-11-yl)-N-methylmethanamine (5) and 1-(1,8-dichloro-9,10-dihydro-9,10-ethanoanthracen-11-yl)-N-methylmethanamine (6) as a homologue of the anxiolytic and antidepressant drugs benzoctamine and maprotiline were described. The key intermediate aldehydes (3) and (4) were successfully synthesized via a [4 + 2] cycloaddition between acrolein and 1,8-dichloroanthracene. The synthesized compounds were investigated for antidepressant activity using the forced swimming test. Compounds (5), (6) and (3) showed significant reduction in the mice immobility indicating significant antidepressant effects. These compounds significantly reduced the immobility times at a dose 80 mg/kg by 84.0%, 86.7% and 71.1% respectively.
Highlights
Depression is the most common psychiatric disorder and is among the 10 leading causes of morbidity and mortality worldwide [1,2]
Recent studies have indicated that depression occurs in all ethnic, racial, and socioeconomic groups and can occur at any age, from childhood to old age. These studies concluded that depression is a common psychiatric disorder in the general population
Benzoctamine is primarily an anxiolytic drug that exhibits antagonistic effects on norepinephrine, while maprotiline is an antidepressant and anxiolytic drug that is useful as a norepinephrine uptake inhibitor
Summary
Depression is the most common psychiatric disorder and is among the 10 leading causes of morbidity and mortality worldwide [1,2]. Recent studies have indicated that depression occurs in all ethnic, racial, and socioeconomic groups and can occur at any age, from childhood to old age. These studies concluded that depression is a common psychiatric disorder in the general population. The tetracyclic drugs benzoctamine 1-(9,10-dihydro-9,10-ethanoanthracen-9-yl)-N-methylmethanamine and maprotiline 3-(9,10-dihydro-9,10-ethanoanthracen-9-yl)-N-methylpropanamine are bridged anthracene compounds that do not possess halogen atoms [8]. Despite their structural similarity, benzoctamine is primarily an anxiolytic drug that exhibits antagonistic effects on norepinephrine, while maprotiline is an antidepressant and anxiolytic drug that is useful as a norepinephrine uptake inhibitor. Molecules 2016, 21, 61 of 6 nce the insertion of a chlorine atoms in the maprotiline related compounds could 2be a small chang or a big improvement aiding in the development of more potent analogues
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