{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,4,20]],"date-time":"2026-04-20T13:32:40Z","timestamp":1776691960883,"version":"3.51.2"},"reference-count":76,"publisher":"MDPI AG","issue":"21","license":[{"start":{"date-parts":[[2022,10,22]],"date-time":"2022-10-22T00:00:00Z","timestamp":1666396800000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"funder":[{"name":"Funds for Statutory Activity of the Medical University of Gda\u0144sk","award":["ST-020038\/07"],"award-info":[{"award-number":["ST-020038\/07"]}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Molecules"],"abstract":"<jats:p>A series of copper(II) complexes of 2-imino-2H-chromen-3-yl-1,3,5-triazines 2a-h, 3-(benzoxazol-2-yl)-2H-chromen-2-imines 4a-b, and 3-(benzothiazol-2-yl)-2H-chromen-2-imines 6a-c were obtained by reacting of appropriate 2-iminocoumarin ligands L1a-h, L3a-b, and L5a-c with 3-fold molar excess of copper(II) chloride. The structure of these compounds was confirmed by IR spectroscopy, elemental analysis, and single-crystal X-ray diffraction data (2f, 2g, 2h, and 6c). All the synthesized complexes were screened for their activity against five human cancer cell lines: DAN-G, A-427, LCLC-103H, SISO, and RT-4 by using a crystal violet microtiter plate assay and relationships between structure and in vitro cytotoxic activity are discussed. The coordination of 2-iminocoumarins with copper(II) ions resulted in complexes 2a-h, 4a-b, and 6a-c with significant inhibitory properties toward tested tumor cell lines with IC50 values ranging from 0.04 \u03bcM to 15.66 \u03bcM. In comparison to the free ligands L1a-h, L3a-b, and L5a-c, the newly prepared Cu(II) complexes often displayed increased activity. In the series of copper(II) complexes of 2-imino-2H-chromen-3-yl-1,3,5-triazines 2a-h the most potent compound 2g contained a 4-phenylpiperazine moiety at position 6 of the 1,3,5-triazine ring and an electron-donating diethylamino group at position 7\u2032 of the 2-iminocoumarin scaffold. Among the Cu(II) complexes of 3-(benzoxazol-2-yl)-2H-chromen-2-imines 4a-b and 3-(benzothiazol-2-yl)-2H-chromen-2-imines 6a-c the most active was benzoxazole-2-iminocoumarin 4b that also possessed a diethylamino group at position 7\u2032 of the 2-iminocoumarin moiety. Moreover, compound 4b was found to be the most prominent agent and displayed the higher potency than cisplatin against tested cell lines.<\/jats:p>","DOI":"10.3390\/molecules27217155","type":"journal-article","created":{"date-parts":[[2022,10,24]],"date-time":"2022-10-24T08:19:06Z","timestamp":1666599546000},"page":"7155","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":10,"title":["Synthesis, Structure and Cytotoxic Properties of Copper(II) Complexes of 2-Iminocoumarins Bearing a 1,3,5-Triazine or Benzoxazole\/Benzothiazole Moiety"],"prefix":"10.3390","volume":"27","author":[{"given":"Anna","family":"Makowska","sequence":"first","affiliation":[{"name":"Department of Chemical Technology of Drugs, Faculty of Pharmacy, Medical University of Gda\u0144sk, Al. Gen. J. Hallera 107, 80-416 Gdansk, Poland"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Franciszek","family":"S\u0105czewski","sequence":"additional","affiliation":[{"name":"Department of Chemical Technology of Drugs, Faculty of Pharmacy, Medical University of Gda\u0144sk, Al. Gen. J. Hallera 107, 80-416 Gdansk, Poland"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-9589-8241","authenticated-orcid":false,"given":"Patrick J.","family":"Bednarski","sequence":"additional","affiliation":[{"name":"Department of Pharmaceutical and Medicinal Chemistry, Institute of Pharmacy, University of Greifswald, F.-L. Jahn Strasse 17, D-17489 Greifswald, Germany"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-8249-7193","authenticated-orcid":false,"given":"Maria","family":"Gdaniec","sequence":"additional","affiliation":[{"name":"Faculty of Chemistry, Adam Mickiewicz University, ul. Uniwersytetu Pozna\u0144skiego 8, 61-614 Pozna\u0144, Poland"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-5234-1198","authenticated-orcid":false,"given":"\u0141ukasz","family":"Balewski","sequence":"additional","affiliation":[{"name":"Department of Chemical Technology of Drugs, Faculty of Pharmacy, Medical University of Gda\u0144sk, Al. Gen. J. Hallera 107, 80-416 Gdansk, Poland"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-6024-9305","authenticated-orcid":false,"given":"Magdalena","family":"Warmbier","sequence":"additional","affiliation":[{"name":"Department of Chemical Technology of Drugs, Faculty of Pharmacy, Medical University of Gda\u0144sk, Al. Gen. J. Hallera 107, 80-416 Gdansk, Poland"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-2792-9229","authenticated-orcid":false,"given":"Anita","family":"Kornicka","sequence":"additional","affiliation":[{"name":"Department of Chemical Technology of Drugs, Faculty of Pharmacy, Medical University of Gda\u0144sk, Al. Gen. J. Hallera 107, 80-416 Gdansk, Poland"}],"role":[{"role":"author","vocabulary":"crossref"}]}],"member":"1968","published-online":{"date-parts":[[2022,10,22]]},"reference":[{"key":"ref_1","first-page":"141","article-title":"Drug resistance and combating drug resistance in cancer","volume":"2","author":"Wang","year":"2019","journal-title":"Cancer Drug Resist"},{"key":"ref_2","doi-asserted-by":"crossref","first-page":"6645","DOI":"10.1039\/C8DT00838H","article-title":"The side effects of platinum-based chemotherapy drugs: A review for chemists","volume":"47","author":"Oun","year":"2018","journal-title":"Dalton Trans."},{"key":"ref_3","doi-asserted-by":"crossref","first-page":"343","DOI":"10.3389\/fphar.2020.00343","article-title":"The drug-resistance mechanisms of five platinum-based antitumor agents","volume":"11","author":"Zhou","year":"2020","journal-title":"Front. 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