{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2025,10,12]],"date-time":"2025-10-12T04:17:40Z","timestamp":1760242660483,"version":"build-2065373602"},"reference-count":11,"publisher":"MDPI AG","issue":"1","license":[{"start":{"date-parts":[[2016,1,5]],"date-time":"2016-01-05T00:00:00Z","timestamp":1451952000000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Molecules"],"abstract":"<jats:p>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.<\/jats:p>","DOI":"10.3390\/molecules21010061","type":"journal-article","created":{"date-parts":[[2016,1,6]],"date-time":"2016-01-06T02:18:12Z","timestamp":1452046692000},"page":"61","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":10,"title":["Synthesis of Chlorinated Tetracyclic Compounds and Testing for Their Potential Antidepressant Effect in Mice"],"prefix":"10.3390","volume":"21","author":[{"given":"Usama","family":"Karama","sequence":"first","affiliation":[{"name":"Chemistry Department, College of Science, King Saud University, P. O. Box 2455 Riyadh 11451, Saudi Arabia"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Mujeeb","family":"Sultan","sequence":"additional","affiliation":[{"name":"Chemistry Department, College of Science, King Saud University, P. O. Box 2455 Riyadh 11451, Saudi Arabia"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Abdulrahman","family":"Almansour","sequence":"additional","affiliation":[{"name":"Chemistry Department, College of Science, King Saud University, P. O. Box 2455 Riyadh 11451, Saudi Arabia"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Kamal","family":"El-Taher","sequence":"additional","affiliation":[{"name":"Department of Pharmacology, College of Pharmacy, King Saud University, P. O. Box 2457, Riyadh 11451, Saudi Arabia"}],"role":[{"role":"author","vocabulary":"crossref"}]}],"member":"1968","published-online":{"date-parts":[[2016,1,5]]},"reference":[{"key":"ref_1","doi-asserted-by":"crossref","first-page":"1043","DOI":"10.1016\/j.jpsychires.2010.03.017","article-title":"The epidemiology of major depression and ethnicity in the united states","volume":"44","author":"Tarraf","year":"2010","journal-title":"J. Psychiatr. Res."},{"key":"ref_2","doi-asserted-by":"crossref","first-page":"415","DOI":"10.1016\/j.amepre.2005.02.009","article-title":"Assessing the burden of disease in the united states using disability-adjusted life years","volume":"28","author":"McKenna","year":"2005","journal-title":"Am. J. Prev. Med."},{"key":"ref_3","doi-asserted-by":"crossref","first-page":"204","DOI":"10.1002\/msj.20094","article-title":"Physical exercise and depression","volume":"76","author":"Collins","year":"2009","journal-title":"Mt. Sinai J. Med."},{"key":"ref_4","doi-asserted-by":"crossref","first-page":"2267","DOI":"10.1039\/c0cs00177e","article-title":"Halogen bonding in halocarbon\u2013protein complexes: A structural survey","volume":"40","author":"Parisini","year":"2011","journal-title":"Chem. Soc. Rev."},{"key":"ref_5","doi-asserted-by":"crossref","first-page":"3547","DOI":"10.1039\/c2cs15292d","article-title":"Halogen bonding in solution","volume":"41","author":"Erdelyi","year":"2012","journal-title":"Chem. Soc. Rev."},{"key":"ref_6","doi-asserted-by":"crossref","first-page":"981","DOI":"10.1039\/C2CC37584B","article-title":"Plugging the explicit \u03c3-holes in molecular docking","volume":"49","author":"Hobza","year":"2013","journal-title":"Chem. Commun."},{"key":"ref_7","doi-asserted-by":"crossref","first-page":"5015","DOI":"10.1007\/s00894-013-2005-7","article-title":"A knowledge-based halogen bonding scoring function for predicting protein-ligand interactions","volume":"19","author":"Liu","year":"2013","journal-title":"J. Mol. Model."},{"key":"ref_8","doi-asserted-by":"crossref","first-page":"1385","DOI":"10.1002\/hlca.19690520602","article-title":"Synthese und eigenschaften von 1-aminoalkyl-dibenzo[b,e]bicyclo[2.2.2]octadienen","volume":"52","author":"Wilhelm","year":"1969","journal-title":"Helv. Chim. Acta"},{"key":"ref_9","unstructured":"Karama, U.S., Sultan, M.A.S., EL-Tahir, K.E.H., and Almansour, A.I. (2015). Antidepressant Compounds. (9125866 B1), U.S. Patent."},{"key":"ref_10","doi-asserted-by":"crossref","first-page":"1807","DOI":"10.1021\/jo01298a013","article-title":"Reactions of the 1,8-diphenylanthracene system","volume":"45","author":"House","year":"1980","journal-title":"J. Org. Chem."},{"key":"ref_11","doi-asserted-by":"crossref","first-page":"373","DOI":"10.1007\/s00213-002-1335-4","article-title":"Antidepressant-like effects in various mice strains in the forced swimming test","volume":"166","author":"David","year":"2003","journal-title":"Psychopharmacology"}],"container-title":["Molecules"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/www.mdpi.com\/1420-3049\/21\/1\/61\/pdf","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,10,11]],"date-time":"2025-10-11T19:17:17Z","timestamp":1760210237000},"score":1,"resource":{"primary":{"URL":"https:\/\/www.mdpi.com\/1420-3049\/21\/1\/61"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2016,1,5]]},"references-count":11,"journal-issue":{"issue":"1","published-online":{"date-parts":[[2016,1]]}},"alternative-id":["molecules21010061"],"URL":"https:\/\/doi.org\/10.3390\/molecules21010061","relation":{},"ISSN":["1420-3049"],"issn-type":[{"type":"electronic","value":"1420-3049"}],"subject":[],"published":{"date-parts":[[2016,1,5]]}}}