{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,8,26]],"date-time":"2026-08-26T06:08:42Z","timestamp":1787724522463,"version":"build-2784847793"},"reference-count":88,"publisher":"MDPI AG","issue":"1","license":[{"start":{"date-parts":[[2021,12,26]],"date-time":"2021-12-26T00:00:00Z","timestamp":1640476800000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"funder":[{"name":"INGA MU, with the support of the Specific University Research Grant, as provided by the Ministry of Edu-cation, Youth and Sports of the Czech Republic in the year 2020","award":["MUNI\/A\/1202\/2020"],"award-info":[{"award-number":["MUNI\/A\/1202\/2020"]}]},{"DOI":"10.13039\/501100005357","name":"Slovak Research and Development Agency","doi-asserted-by":"publisher","award":["APVV-18-0302"],"award-info":[{"award-number":["APVV-18-0302"]}],"id":[{"id":"10.13039\/501100005357","id-type":"DOI","asserted-by":"publisher"}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["IJMS"],"abstract":"<jats:p>A series of 1,3,5-triazinyl aminobenzenesulfonamides substituted by aminoalcohol, aminostilbene, and aminochalcone structural motifs was synthesized as potential human carbonic anhydrase (hCA) inhibitors. The compounds were evaluated on their inhibition of tumor-associated hCA IX and hCA XII, hCA VII isoenzyme present in the brain, and physiologically important hCA I and hCA II. While the test compounds had only a negligible effect on physiologically important isoenzymes, many of the studied compounds significantly affected the hCA IX isoenzyme. Several compounds showed activity against hCA XII; (E)-4-{2-[(4-[(2,3-dihydroxypropyl)amino]-6-[(4-styrylphenyl)amino]-1,3,5-triazin-2-yl)amino]ethyl}benzenesulfonamide (31) and (E)-4-{2-[(4-[(4-hydroxyphenyl)amino]-6-[(4-styrylphenyl)amino]-1,3,5-triazin-2-yl)amino]ethyl}benzenesulfonamide (32) were the most effective inhibitors with KIs = 4.4 and 5.9 nM, respectively. In addition, the compounds were tested against vancomycin-resistant Enterococcus faecalis (VRE) isolates. (E)-4-[2-({4-[(4-cinnamoylphenyl)amino]-6-[(4-hydroxyphenyl)amino]-1,3,5-triazin-2-yl}amino)ethyl]benzenesulfonamide (21) (MIC = 26.33 \u00b5M) and derivative 32 (MIC range 13.80\u201355.20 \u00b5M) demonstrated the highest activity against all tested strains. The most active compounds were evaluated for their cytotoxicity against the Human Colorectal Tumor Cell Line (HCT116 p53 +\/+). Only 4,4\u2019-[(6-chloro-1,3,5-triazin-2,4-diyl)bis(iminomethylene)]dibenzenesulfonamide (7) and compound 32 demonstrated an IC50 of ca. 6.5 \u03bcM; otherwise, the other selected derivatives did not show toxicity at concentrations up to 50 \u00b5M. The molecular modeling and docking of active compounds into various hCA isoenzymes, including bacterial carbonic anhydrase, specifically \u03b1-CA present in VRE, was performed to try to outline a possible mechanism of selective anti-VRE activity.<\/jats:p>","DOI":"10.3390\/ijms23010231","type":"journal-article","created":{"date-parts":[[2021,12,27]],"date-time":"2021-12-27T01:00:54Z","timestamp":1640566854000},"page":"231","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":10,"title":["Novel 1,3,5-Triazinyl Aminobenzenesulfonamides Incorporating Aminoalcohol, Aminochalcone and Aminostilbene Structural Motifs as Potent Anti-VRE Agents, and Carbonic Anhydrases I, II, VII, IX, and XII Inhibitors"],"prefix":"10.3390","volume":"23","author":[{"given":"Eva","family":"Havr\u00e1nkov\u00e1","sequence":"first","affiliation":[{"name":"Department of Chemical Drugs, Faculty of Pharmacy, Masaryk University, Palack\u00e9ho 1-3, 612 42 Brno, Czech Republic"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-8229-414X","authenticated-orcid":false,"given":"Vladim\u00edr","family":"Garaj","sequence":"additional","affiliation":[{"name":"Department of Pharmaceutical chemistry, Faculty of Pharmacy, Comenius University, Odbojarov 10, 832 32 Bratislava, Slovakia"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"\u0160\u00e1rka","family":"Mascaretti","sequence":"additional","affiliation":[{"name":"Czech Advanced Technology and Research Institute, Palacky University, Slechtitelu 27, 783 71 Olomouc, Czech Republic"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-1470-7192","authenticated-orcid":false,"given":"Andrea","family":"Angeli","sequence":"additional","affiliation":[{"name":"Section of Farmaceutical and Neutraceutical Sciences, Neurofarba Department, University of Florence, 50019 Sesto Fiorentino, Italy"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Zuzana","family":"Sold\u00e1nov\u00e1","sequence":"additional","affiliation":[{"name":"Department of Molecular Pharmacy, Faculty of Pharmacy, Masaryk University, Palack\u00e9ho 1-3, 612 42 Brno, Czech Republic"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Miroslav","family":"Kemka","sequence":"additional","affiliation":[{"name":"Department of Pharmaceutical chemistry, Faculty of Pharmacy, Comenius University, Odbojarov 10, 832 32 Bratislava, Slovakia"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Jozef","family":"Moty\u010dka","sequence":"additional","affiliation":[{"name":"Department of Pharmaceutical Analysis and Nuclear Pharmacy, Faculty of Pharmacy, Comenius University, Odbojarov 10, 832 32 Bratislava, Slovakia"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Marie","family":"Br\u00e1zdov\u00e1","sequence":"additional","affiliation":[{"name":"Department of Molecular Pharmacy, Faculty of Pharmacy, Masaryk University, Palack\u00e9ho 1-3, 612 42 Brno, Czech Republic"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Jozef","family":"Cs\u00f6llei","sequence":"additional","affiliation":[{"name":"Department of Chemical Drugs, Faculty of Pharmacy, Masaryk University, Palack\u00e9ho 1-3, 612 42 Brno, Czech Republic"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-2003-9052","authenticated-orcid":false,"given":"Josef","family":"Jamp\u00edlek","sequence":"additional","affiliation":[{"name":"Department of Chemical Biology, Faculty of Science, Palacky University, Slechtitelu 27, 783 71 Olomouc, Czech Republic"},{"name":"Institute of Neuroimmunology, Slovak Academy of Sciences, D\u00fabravska Cesta 9, 845 10 Bratislava, Slovakia"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-4262-0323","authenticated-orcid":false,"given":"Claudiu T.","family":"Supuran","sequence":"additional","affiliation":[{"name":"Section of Farmaceutical and Neutraceutical Sciences, Neurofarba Department, University of Florence, 50019 Sesto Fiorentino, Italy"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"1968","published-online":{"date-parts":[[2021,12,26]]},"reference":[{"key":"ref_1","unstructured":"(2021, October 16). 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