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Molecules 2016, 21(1), 61; doi:10.3390/molecules21010061

Synthesis of Chlorinated Tetracyclic Compounds and Testing for Their Potential Antidepressant Effect in Mice

Chemistry Department, College of Science, King Saud University, P. O. Box 2455 Riyadh 11451, Saudi Arabia
Department of Pharmacology, College of Pharmacy, King Saud University, P. O. Box 2457, Riyadh 11451, Saudi Arabia
Author to whom correspondence should be addressed.
Academic Editor: Maria Emília de Sousa
Received: 20 November 2015 / Revised: 30 December 2015 / Accepted: 31 December 2015 / Published: 5 January 2016
(This article belongs to the Section Organic Synthesis)
View Full-Text   |   Download PDF [443 KB, uploaded 5 January 2016]   |  


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. View Full-Text
Keywords: chlorinated tetracyclic; antidepressants; synthesis; forced swimming test chlorinated tetracyclic; antidepressants; synthesis; forced swimming test

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Karama, U.; Sultan, M.A.; Almansour, A.I.; El-Taher, K.E. Synthesis of Chlorinated Tetracyclic Compounds and Testing for Their Potential Antidepressant Effect in Mice. Molecules 2016, 21, 61.

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