title: Synthesis of Chlorinated Tetracyclic Compounds and Testing for Their Potential Antidepressant Effect in Mice.
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.
authors.affiliation: Chemistry Department, College of Science, King Saud University, P. O. Box 2455 Riyadh 11451, Saudi Arabia. Karama@ksu.edu.sa.
authors.forename: Usama
authors.initials: U
authors.lastname: Karama
authors.affiliation: Chemistry Department, College of Science, King Saud University, P. O. Box 2455 Riyadh 11451, Saudi Arabia. Alhosami1983@yahoo.co.uk.
authors.forename: Mujeeb A
authors.initials: MA
authors.lastname: Sultan
authors.affiliation: Chemistry Department, College of Science, King Saud University, P. O. Box 2455 Riyadh 11451, Saudi Arabia. almansor@ksu.edu.sa.
authors.forename: Abdulrahman I
authors.initials: AI
authors.lastname: Almansour
authors.affiliation: Department of Pharmacology, College of Pharmacy, King Saud University, P. O. Box 2457, Riyadh 11451, Saudi Arabia. eeltahir@ksu.edu.sa.
authors.forename: Kamal Eldin
authors.initials: KE
authors.lastname: El-Taher
mesh_terms: D000818:Animals; D000873:Anthracenes / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D014151:Anti-Anxiety Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D000928:Antidepressive Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D006843:Hydrocarbons, Chlorinated / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D046353:Immobility Response, Tonic / Q000187:drug effects; D008376:Maprotiline / Q000737:chemistry / Q000494:pharmacology; D051379:Mice; D015394:Molecular Structure; D013550:Swimming
chemical_list: C000611410:1-(1,8-dichloro-9,10-dihydro-9,10-ethanoanthracen-11-yl)-N-methylmethanamine; C000611409:1-(4,5-dichloro-9,10-dihydro-9,10-ethanoanthracen-11-yl)-N-methylmethanamine; D000873:Anthracenes; D014151:Anti-Anxiety Agents; D000928:Antidepressive Agents; D006843:Hydrocarbons, Chlorinated; D008376:Maprotiline; C100247:benzoctamine
keywords: antidepressants; chlorinated tetracyclic; forced swimming test; synthesis