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A dded 2-aminobenzophenone (3.0 mmol) refluxed with citric acid (1.5 mmol) in dioxane to the flask, then slowly added to acetylacetone (3.0 mmol) and refluxed for 12 h. The reaction was identified by TLC. After completion of the reaction, sodium hydroxide solution was added to the reaction mixture. The precipitate separated by filtration and washed with 0.2 mol\/mL HCl water. The crude product was purified by silica gel column. Synthesis of 2-methyl-4phenylquinolin-chalcone derivatives 2a-2x A mixture of 1-(2-methyl-4-phenylquinolin-3-yl)ethanone (1.5 mmol) and different aldehydes (1.5 mmol) in ethanolic solution of NaOH was stirred at room temperature for 24 h. The reaction was identified by TLC. After completion of reaction, the reaction mixture was dumped into water and extracted with ether. The extract was repeatedly washed with water, dried over anhydrous sodium sulfate and concentration to give target compounds 2a-2x, which was crystallized from ethanol (Scheme 1). (E)-3-(2-fluorophenyl)-1-(2-methyl-4-phenylquinolin-3-yl)prop-2-en-1-one (2a). Yield: 72.1 %; yellow solid. mp 120.1-123.0 \u00b0C. IR (KBr) cm-1: 2930, 1644, 1564. 1H NMR (CDCl3, DMSO-d6, 300 MHz): 2.44 (s, 3H, quinolin-CH3), 7.33 (d, 1H, J = 15.1 Hz, -CO-CH=CH), 7.04-7.62 (m, 4H, ph-H), 7.15-7.51 (m, 5H, ph-H), 7.59-8.08 (m, 4H, ph-H), 7.72 (d, 1H, J = 15.1 Hz, -CH=CH). 13C NMR (CDCl3, DMSO-d6, 75 MHz): 28.75 (CH3), 120.78 (CH), 121.07 (CH), 131.04 (CH), 131.51 (CH), 133.25 (CH), 133.52 (CH), 133.69 (CH), 134.84 (CH), 135.02 (CH), 139.89 (C), 149.94 (C), 152.41 (C), 159.27 (C), 201.85 (C). HRMS (m\/z): [M+H]+ calcd. for C25H18FNO: 367.41; found: 367.38. Purity: 98.6 % by HPLC."},{"key":"10.1016\/j.bmcl.2020.127173_b0115","doi-asserted-by":"crossref","first-page":"385","DOI":"10.1016\/0031-9384(86)90110-1","volume":"38","author":"Borsini","year":"1986","journal-title":"Physiol Behav."},{"key":"10.1016\/j.bmcl.2020.127173_b0120","first-page":"1574","volume":"15","author":"Gao","year":"2018","journal-title":"Exp Ther Med."},{"key":"10.1016\/j.bmcl.2020.127173_b0125","doi-asserted-by":"crossref","first-page":"106","DOI":"10.22365\/jpsych.2016.272.106","volume":"27L","author":"Boufidou","year":"2016","journal-title":"Psychiatriki."},{"key":"10.1016\/j.bmcl.2020.127173_b0130","doi-asserted-by":"crossref","first-page":"1179","DOI":"10.1007\/s12010-016-2277-3","volume":"181","author":"Ismail","year":"2017","journal-title":"Appl Biochem Biotechnol."},{"key":"10.1016\/j.bmcl.2020.127173_b0135","doi-asserted-by":"crossref","first-page":"509","DOI":"10.1016\/j.psychres.2014.11.056","volume":"225","author":"Xu","year":"2015","journal-title":"Psychiatr Res."},{"key":"10.1016\/j.bmcl.2020.127173_b0140","doi-asserted-by":"crossref","first-page":"81","DOI":"10.1515\/jbcpp-2016-0173","volume":"29","author":"Al Mahmud","year":"2018","journal-title":"J Basic Clin Physiol Pharmacol."},{"key":"10.1016\/j.bmcl.2020.127173_b0145","doi-asserted-by":"crossref","first-page":"1335","DOI":"10.3109\/14756366.2015.1132710","volume":"31","author":"Camadan","year":"2016","journal-title":"J Enzyme Inhib Med Chem."},{"key":"10.1016\/j.bmcl.2020.127173_b0150","doi-asserted-by":"crossref","first-page":"175","DOI":"10.1016\/j.pain.0000000000000018","volume":"156","author":"Miller","year":"2015","journal-title":"Pain"},{"key":"10.1016\/j.bmcl.2020.127173_b0155","doi-asserted-by":"crossref","first-page":"3806","DOI":"10.1016\/j.bmcl.2017.06.063","volume":"27","author":"Lokeshwari","year":"2017","journal-title":"Bioorg Med Chem Lett."},{"key":"10.1016\/j.bmcl.2020.127173_b0160","doi-asserted-by":"crossref","first-page":"3306","DOI":"10.1016\/j.bmc.2012.03.044","volume":"20","author":"El-Sayed","year":"2012","journal-title":"Bioorg Med Chem."}],"container-title":["Bioorganic & Medicinal Chemistry Letters"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/api.elsevier.com\/content\/article\/PII:S0960894X20302705?httpAccept=text\/xml","content-type":"text\/xml","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/api.elsevier.com\/content\/article\/PII:S0960894X20302705?httpAccept=text\/plain","content-type":"text\/plain","content-version":"vor","intended-application":"text-mining"}],"deposited":{"date-parts":[[2025,10,18]],"date-time":"2025-10-18T07:32:56Z","timestamp":1760772776000},"score":1,"resource":{"primary":{"URL":"https:\/\/linkinghub.elsevier.com\/retrieve\/pii\/S0960894X20302705"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2020,6]]},"references-count":32,"journal-issue":{"issue":"11","published-print":{"date-parts":[[2020,6]]}},"alternative-id":["S0960894X20302705"],"URL":"https:\/\/doi.org\/10.1016\/j.bmcl.2020.127173","relation":{},"ISSN":["0960-894X"],"issn-type":[{"value":"0960-894X","type":"print"}],"subject":[],"published":{"date-parts":[[2020,6]]},"assertion":[{"value":"Elsevier","name":"publisher","label":"This article is maintained by"},{"value":"Screening of chalcone analogs with anti-depressant, anti-inflammatory, analgesic, and COX-2-inhibiting effects","name":"articletitle","label":"Article Title"},{"value":"Bioorganic & Medicinal Chemistry Letters","name":"journaltitle","label":"Journal Title"},{"value":"https:\/\/doi.org\/10.1016\/j.bmcl.2020.127173","name":"articlelink","label":"CrossRef DOI link to publisher maintained version"},{"value":"article","name":"content_type","label":"Content Type"},{"value":"\u00a9 2020 Elsevier Ltd. 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