{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,5,15]],"date-time":"2026-05-15T23:15:24Z","timestamp":1778886924423,"version":"3.51.4"},"reference-count":53,"publisher":"MDPI AG","issue":"18","license":[{"start":{"date-parts":[[2024,9,12]],"date-time":"2024-09-12T00:00:00Z","timestamp":1726099200000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"funder":[{"name":"Medical University of Silesia in Katowice, Poland","award":["BNW-1-100\/K\/4\/F"],"award-info":[{"award-number":["BNW-1-100\/K\/4\/F"]}]},{"name":"University of Silesian in Katowice","award":["BNW-1-100\/K\/4\/F"],"award-info":[{"award-number":["BNW-1-100\/K\/4\/F"]}]},{"name":"PBKM S.A. FamiCord Group","award":["BNW-1-100\/K\/4\/F"],"award-info":[{"award-number":["BNW-1-100\/K\/4\/F"]}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Molecules"],"abstract":"<jats:p>In this work, the synthesis, structural analysis and anticancer properties of 5-methyl-9-trifluoromethyl-12H-quino[3,4-b][1,4]benzothiazinium chloride (3) are described. Compound 3 was synthesized by reacting 1-methyl-4-butylthio-3-(benzoylthio)quinolinium chloride with 4-(trifluoromethyl)aniline, respectively. The structure of the resulting product was determined using 1H-NMR and 13C-NMR spectroscopy as well as HR-MS spectrometry. The spatial geometry of agent 3 and the arrangement of molecules in the crystal (unit cell) were also confirmed using X-ray diffraction. The tetracyclic quinobenzothiazinium system is fairly planar because the dihedral angle between the planes formed by the benzene ring and the quinoline system is 173.47\u00b0. In order to obtain insight into the electronic charge distribution of the investigated molecule, electronic structure calculations employing the Density Functional Theory (DFT) were performed. Moreover, antiproliferative activity against a set of pancreatic cancer cell lines was tested, with compound 3 showing IC50 values against human primary pancreatic adenocarcinoma BxPC-3 and human epithelioid pancreatic carcinoma Panc-1 of 0.051 \u00b5M and 0.066 \u00b5M, respectively. The IC50 value of cytotoxicity\/cell viability of the investigated compound assessed on normal human lung fibroblasts WI38 was 0.36 \u00b5M.<\/jats:p>","DOI":"10.3390\/molecules29184337","type":"journal-article","created":{"date-parts":[[2024,9,12]],"date-time":"2024-09-12T10:15:27Z","timestamp":1726136127000},"page":"4337","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":2,"title":["Synthesis and Structure of 5-Methyl-9-(trifluoromethyl)-12H-quino[3,4-b][1,4]benzothiazinium Chloride as Anticancer Agent"],"prefix":"10.3390","volume":"29","author":[{"ORCID":"https:\/\/orcid.org\/0000-0002-7841-3097","authenticated-orcid":false,"given":"Andrzej","family":"Zieba","sequence":"first","affiliation":[{"name":"Department of Organic Chemistry, Faculty of Pharmaceutical Sciences in Sosnowiec, Medical University of Silesia, Jagiellonska 4, 41-200 Sosnowiec, Poland"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Violetta","family":"Kozik","sequence":"additional","affiliation":[{"name":"Institute of Chemistry, University of Silesia, Szkolna 9, 40-007 Katowice, Poland"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-6702-0773","authenticated-orcid":false,"given":"Kinga","family":"Suwinska","sequence":"additional","affiliation":[{"name":"Faculty of Mathematics and Natural Sciences, Cardinal Stefan Wyszynski University, K. Woycickiego 1\/3, 01-938 Warszawa, Poland"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-3315-428X","authenticated-orcid":false,"given":"Agata","family":"Kawulok","sequence":"additional","affiliation":[{"name":"Institute of Chemistry, University of Silesia, Szkolna 9, 40-007 Katowice, Poland"},{"name":"Department of Bone Marrow Transplantation and Oncohematology, Maria Sklodowska-Curie National Research Institute of Oncology, Gliwice Branch, ul. Wybrzeze Armii Krajowej 15, 44-101 Gliwice, Poland"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-5166-696X","authenticated-orcid":false,"given":"Tadeusz","family":"Pluta","sequence":"additional","affiliation":[{"name":"Institute of Chemistry, University of Silesia, Szkolna 9, 40-007 Katowice, Poland"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-2003-9052","authenticated-orcid":false,"given":"Josef","family":"Jampilek","sequence":"additional","affiliation":[{"name":"Institute of Chemistry, University of Silesia, Szkolna 9, 40-007 Katowice, Poland"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-9842-1289","authenticated-orcid":false,"given":"Andrzej","family":"Bak","sequence":"additional","affiliation":[{"name":"Institute of Chemistry, University of Silesia, Szkolna 9, 40-007 Katowice, Poland"}],"role":[{"role":"author","vocabulary":"crossref"}]}],"member":"1968","published-online":{"date-parts":[[2024,9,12]]},"reference":[{"key":"ref_1","doi-asserted-by":"crossref","unstructured":"Posso, M.C., Domingues, F.C., Ferreira, S., and Silvestre, S. 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