{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,7,3]],"date-time":"2026-07-03T21:43:02Z","timestamp":1783114982922,"version":"3.54.6"},"reference-count":86,"publisher":"MDPI AG","issue":"17","license":[{"start":{"date-parts":[[2024,8,26]],"date-time":"2024-08-26T00:00:00Z","timestamp":1724630400000},"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-1-013\/N\/3\/F"],"award-info":[{"award-number":["BNW-1-013\/N\/3\/F"]}]},{"name":"Medical University of Silesia in Katowice, Poland","award":["PCN-1-048\/K\/2\/F"],"award-info":[{"award-number":["PCN-1-048\/K\/2\/F"]}]},{"name":"Medical University of Silesia in Katowice, Poland","award":["2018\/31\/B\/NZ7\/02122"],"award-info":[{"award-number":["2018\/31\/B\/NZ7\/02122"]}]},{"name":"Polish National Science Center","award":["BNW-1-013\/N\/3\/F"],"award-info":[{"award-number":["BNW-1-013\/N\/3\/F"]}]},{"name":"Polish National Science Center","award":["PCN-1-048\/K\/2\/F"],"award-info":[{"award-number":["PCN-1-048\/K\/2\/F"]}]},{"name":"Polish National Science Center","award":["2018\/31\/B\/NZ7\/02122"],"award-info":[{"award-number":["2018\/31\/B\/NZ7\/02122"]}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Molecules"],"abstract":"<jats:p>A series of new unique acetylene derivatives of 8-hydroxy- and 8-methoxyquinoline- 5-sulfonamide 3a\u2013f and 6a\u2013f were prepared by reactions of 8-hydroxy- and 8-methoxyquinoline- 5-sulfonyl chlorides with acetylene derivatives of amine. A series of new hybrid systems containing quinoline and 1,2,3-triazole systems 7a\u2013h were obtained by reactions of acetylene derivatives of quinoline-5-sulfonamide 6a\u2013d with organic azides. The structures of the obtained compounds were confirmed by 1H and 13C NMR spectroscopy and HR-MS spectrometry. The obtained quinoline derivatives 3a\u2013f and 6a\u2013f and 1,2,3-triazole derivatives 7a\u2013h were tested for their anticancer and antimicrobial activity. Human amelanotic melanoma cells (C-32), human breast adenocarcinoma cells (MDA-MB-231), and human lung adenocarcinoma cells (A549) were selected as tested cancer lines, while cytotoxicity was investigated on normal human dermal fibroblasts (HFF-1). All the compounds were also tested against reference strains Staphylococcus aureus ATCC 29213 and Enterococcus faecalis ATCC 29212 and representatives of multidrug-resistant clinical isolates of methicillin-resistant S. aureus (MRSA) and vancomycin-resistant E. faecalis. Only the acetylene derivatives of 8-hydroxyquinoline-5-sulfonamide 3a\u2013f were shown to be biologically active, and 8-hydroxy-N-methyl-N-(prop-2-yn-1-yl)quinoline-5-sulfonamide (3c) showed the highest activity against all three cancer lines and MRSA isolates. Its efficacies were comparable to those of cisplatin\/doxorubicin and oxacillin\/ciprofloxacin. In the non-cancer HFF-1 line, the compound showed no toxicity up to an IC50 of 100 \u00b5M. In additional tests, compound 3c decreased the expression of H3, increased the transcriptional activity of cell cycle regulators (P53 and P21 proteins), and altered the expression of BCL-2 and BAX genes in all cancer lines. The unsubstituted phenolic group at position 8 of the quinoline is the key structural fragment necessary for biological activity.<\/jats:p>","DOI":"10.3390\/molecules29174044","type":"journal-article","created":{"date-parts":[[2024,8,27]],"date-time":"2024-08-27T03:51:06Z","timestamp":1724730666000},"page":"4044","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":17,"title":["Design, Synthesis, and Anticancer and Antibacterial Activities of Quinoline-5-Sulfonamides"],"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":[{"vocabulary":"crossref","role":"author"}]},{"given":"Dominika","family":"Pindjakova","sequence":"additional","affiliation":[{"name":"Department of Infectious Diseases and Microbiology, Faculty of Veterinary Medicine, University of Veterinary Sciences Brno, Palackeho 1946\/1, 612 42 Brno, Czech Republic"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-4109-2629","authenticated-orcid":false,"given":"Malgorzata","family":"Latocha","sequence":"additional","affiliation":[{"name":"Department of Cell Biology, Faculty of Pharmaceutical Sciences in Sosnowiec, Medical University of Silesia, Jednosci 9, 41-200 Sosnowiec, Poland"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-0201-525X","authenticated-orcid":false,"given":"Justyna","family":"Plonka-Czerw","sequence":"additional","affiliation":[{"name":"Department of Cell Biology, Faculty of Pharmaceutical Sciences in Sosnowiec, Medical University of Silesia, Jednosci 9, 41-200 Sosnowiec, Poland"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Dariusz","family":"Kusmierz","sequence":"additional","affiliation":[{"name":"Department of Cell Biology, Faculty of Pharmaceutical Sciences in Sosnowiec, Medical University of Silesia, Jednosci 9, 41-200 Sosnowiec, Poland"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-5706-4601","authenticated-orcid":false,"given":"Alois","family":"Cizek","sequence":"additional","affiliation":[{"name":"Department of Infectious Diseases and Microbiology, Faculty of Veterinary Medicine, University of Veterinary Sciences Brno, Palackeho 1946\/1, 612 42 Brno, Czech Republic"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"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":[{"vocabulary":"crossref","role":"author"}]}],"member":"1968","published-online":{"date-parts":[[2024,8,26]]},"reference":[{"key":"ref_1","doi-asserted-by":"crossref","first-page":"1921","DOI":"10.2174\/092986712800167356","article-title":"Privileged structures-dream or reality: Preferential organization of azanaphthalene scaffold","volume":"19","author":"Polanski","year":"2012","journal-title":"Curr. 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