{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,10,6]],"date-time":"2026-10-06T04:21:02Z","timestamp":1791260462520,"version":"4.1.0"},"reference-count":21,"publisher":"MDPI AG","issue":"9","license":[{"start":{"date-parts":[[2017,9,19]],"date-time":"2017-09-19T00:00:00Z","timestamp":1505779200000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"funder":[{"name":"This work was supported by the Czech Science Foundation project No. 17-27514Y","award":["17-27514Y"],"award-info":[{"award-number":["17-27514Y"]}]},{"name":"This work was supported by the Charles University (Project SVV 260 414).","award":["SVV 260 414"],"award-info":[{"award-number":["SVV 260 414"]}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Molecules"],"abstract":"<jats:p>The resistance among microbes has brought an urgent need for new drugs. Thus, we synthesized a series of Schiff bases derived from the sulfa drug sulfadiazine and various salicylaldehydes. The resulting 4-[(2-hydroxybenzylidene)amino]-N-(pyrimidin-2-yl)benzene-sulfonamides were characterized and evaluated against Gram-positive and Gram-negative bacteria, yeasts, moulds, Mycobacterium tuberculosis, nontuberculous mycobacteria (M. kansasii, M. avium) and their cytotoxicity was determined. Among bacteria, the genus Staphylococcus, including methicillin-resistant S. aureus, showed the highest susceptibility, with minimum inhibitory concentration values from 7.81 \u00b5M. The growth of Candida sp. and Trichophyton interdigitale was inhibited at concentrations starting from 1.95 \u00b5M. 4-[(2,5-Dihydroxybenzylidene)amino]-N-(pyrimidin-2-yl)-benzenesulfonamide was identified as the most selective Schiff base for these strains with no apparent cytotoxicity and a selectivity index higher than 16. With respect to M. tuberculosis and M. kansasii that were inhibited within the range of 8 to 250 \u00b5M, unsubstituted 4-[(2-hydroxy-benzylidene)amino]-N-(pyrimidin-2-yl)benzenesulfonamide meets the selectivity requirement. In general, dihalogenation of the salicylic moiety improved the antibacterial and antifungal activity but also increased the cytotoxicity, especially with an increasing atomic mass. Some derivatives offer more advantageous properties than the parent sulfadiazine, thus constituting promising hits for further antimicrobial drug development.<\/jats:p>","DOI":"10.3390\/molecules22091573","type":"journal-article","created":{"date-parts":[[2017,9,19]],"date-time":"2017-09-19T11:04:35Z","timestamp":1505819075000},"page":"1573","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":96,"title":["Sulfadiazine Salicylaldehyde-Based Schiff Bases: Synthesis, Antimicrobial Activity and Cytotoxicity"],"prefix":"10.3390","volume":"22","author":[{"given":"Martin","family":"Kr\u00e1tk\u00fd","sequence":"first","affiliation":[{"name":"Department of Organic and Bioorganic Chemistry, Faculty of Pharmacy in Hradec Kr\u00e1lov\u00e9, Charles University, Akademika Heyrovsk\u00e9ho 1203, 500 05 Hradec Kr\u00e1lov\u00e9, Czech Republic"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Magdal\u00e9na","family":"Dzurkov\u00e1","sequence":"additional","affiliation":[{"name":"Department of Chemistry, Faculty of Science, J. E. Purkinje University, \u010cesk\u00e9 ml\u00e1de\u017ee 8, 400 96 \u00dast\u00ed nad Labem, Czech Republic"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-3336-3874","authenticated-orcid":false,"given":"Ji\u0159\u00ed","family":"Janou\u0161ek","sequence":"additional","affiliation":[{"name":"Department of Pharmacology and Toxicology, Faculty of Pharmacy, Charles University, Akademika Heyrovsk\u00e9ho 1203, 500 05 Hradec Kr\u00e1lov\u00e9, Czech Republic"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-5670-7767","authenticated-orcid":false,"given":"Kl\u00e1ra","family":"Kone\u010dn\u00e1","sequence":"additional","affiliation":[{"name":"Department of Biological and Medical Sciences, Faculty of Pharmacy, Charles University, Akademika Heyrovsk\u00e9ho 1203, 500 05 Hradec Kr\u00e1lov\u00e9, Czech Republic"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Franti\u0161ek","family":"Trejtnar","sequence":"additional","affiliation":[{"name":"Department of Pharmacology and Toxicology, Faculty of Pharmacy, Charles University, Akademika Heyrovsk\u00e9ho 1203, 500 05 Hradec Kr\u00e1lov\u00e9, Czech Republic"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Ji\u0159ina","family":"Stola\u0159\u00edkov\u00e1","sequence":"additional","affiliation":[{"name":"Laboratory for Mycobacterial Diagnostics and Tuberculosis, Regional Institute of Public Health in Ostrava, Partyz\u00e1nsk\u00e9 n\u00e1m\u0115st\u00ed 7, 702 00 Ostrava, Czech Republic"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Jarmila","family":"Vin\u0161ov\u00e1","sequence":"additional","affiliation":[{"name":"Department of Organic and Bioorganic Chemistry, Faculty of Pharmacy in Hradec Kr\u00e1lov\u00e9, Charles University, Akademika Heyrovsk\u00e9ho 1203, 500 05 Hradec Kr\u00e1lov\u00e9, Czech Republic"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"1968","published-online":{"date-parts":[[2017,9,19]]},"reference":[{"key":"ref_1","doi-asserted-by":"crossref","first-page":"1","DOI":"10.1016\/j.jare.2010.05.004","article-title":"Schiff bases: A short review of their antimicrobial activities","volume":"2","author":"Modolo","year":"2011","journal-title":"J. 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