{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,6,29]],"date-time":"2026-06-29T19:08:04Z","timestamp":1782760084221,"version":"3.54.5"},"reference-count":20,"publisher":"MDPI AG","issue":"8","license":[{"start":{"date-parts":[[2025,4,21]],"date-time":"2025-04-21T00:00:00Z","timestamp":1745193600000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"funder":[{"name":"Nicolaus Copernicus University","award":["IDUB DEBIUTY4"],"award-info":[{"award-number":["IDUB DEBIUTY4"]}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Molecules"],"abstract":"<jats:p>In recent years, the incidence of acute and chronic inflammatory diseases has increased significantly worldwide, intensifying the search for new therapeutic agents, especially anti-inflammatory drugs. Therefore, the aim of this work was to synthesize, biologically assess, and explore the structure\u2013activity relationships of new compounds containing the cyclohex-1-ene-1-carboxylic acid moiety. Six new derivatives, 2a\u20132f, were synthesized through the reaction of amidrazones 1a\u20131f with 3,4,5,6-tetrahydrophthalic anhydride. Their toxicity was evaluated in cultures of human peripheral blood mononuclear cells (PBMCs). Additionally, their antiproliferative properties and effects on the synthesis of TNF-\u03b1, IL-6, IL-10, and IL-1\u03b2 were assessed in mitogen-stimulated PBMCs. The antimicrobial activity of derivatives 2a\u20132f was determined by measuring the minimal inhibitory concentration (MIC) values against five bacterial strains\u2014Staphylococcus aureus, Mycobacterium smegmatis, Escherichia coli, Yersinia enterocolitica, and Klebsiella pneumoniae\u2014and the fungal strain Candida albicans. All compounds demonstrated antiproliferative activity, with derivatives 2a, 2d, and 2f at a concentration of 100 \u00b5g\/mL being more effective than ibuprofen. Compound 2f strongly inhibited the secretion of TNF-\u03b1 by approximately 66\u201381% at all studied doses (10, 50, and 100 \u00b5g\/mL). Derivative 2b significantly reduced the release of cytokines, including TNF-\u03b1, IL-6, and IL-10, at a high dose (by approximately 92\u201399%). Compound 2c exhibited bacteriostatic activity against S. aureus and M. smegmatis, while derivative 2b selectively inhibited the growth of Y. enterocolitica (MIC = 64 \u00b5g\/mL). Some structure\u2013activity relationships were established for the studied compounds.<\/jats:p>","DOI":"10.3390\/molecules30081853","type":"journal-article","created":{"date-parts":[[2025,4,21]],"date-time":"2025-04-21T03:34:36Z","timestamp":1745206476000},"page":"1853","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":7,"title":["Synthesis, Evaluation of Biological Activity, and Structure\u2013Activity Relationships of New Amidrazone Derivatives Containing Cyclohex-1-ene-1-Carboxylic Acid"],"prefix":"10.3390","volume":"30","author":[{"ORCID":"https:\/\/orcid.org\/0000-0003-1217-879X","authenticated-orcid":false,"given":"Renata","family":"Paprocka","sequence":"first","affiliation":[{"name":"Department of Organic Chemistry, Faculty of Pharmacy, Collegium Medicum in Bydgoszcz, Nicolaus Copernicus University in Toru\u0144, Jurasza Str. 2, 85-089 Bydgoszcz, Poland"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-3307-591X","authenticated-orcid":false,"given":"Jolanta","family":"Kutkowska","sequence":"additional","affiliation":[{"name":"Department of Genetics and Microbiology, Institute of Biological Sciences, Maria Curie-Sk\u0142odowska University, Akademicka Str. 19, 20-033 Lublin, Poland"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Ewelina","family":"Paczkowska","sequence":"additional","affiliation":[{"name":"Department of Immunology, Faculty of Pharmacy, Collegium Medicum in Bydgoszcz, Nicolaus Copernicus University in Toru\u0144, M. Curie-Sklodowska Str. 9, 85-094 Bydgoszcz, Poland"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-6703-0368","authenticated-orcid":false,"given":"Godwin Munroe","family":"Mwaura","sequence":"additional","affiliation":[{"name":"Department of Pharmaceutical Chemistry, Pharmaceutics and Pharmacognosy, Faculty of Health Sciences, University of Nairobi, KNH, Nairobi P.O. Box 2149-00202, Kenya"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-8980-1474","authenticated-orcid":false,"given":"Andrzej","family":"Eljaszewicz","sequence":"additional","affiliation":[{"name":"Centre of Regenerative Medicine, Medical University of Bialystok, Waszyngtona 15 B, 15-269 Bialystok, Poland"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Anna","family":"Helmin-Basa","sequence":"additional","affiliation":[{"name":"Department of Immunology, Faculty of Pharmacy, Collegium Medicum in Bydgoszcz, Nicolaus Copernicus University in Toru\u0144, M. Curie-Sklodowska Str. 9, 85-094 Bydgoszcz, Poland"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"1968","published-online":{"date-parts":[[2025,4,21]]},"reference":[{"key":"ref_1","doi-asserted-by":"crossref","unstructured":"Actor, J.K. (2023). Chapter 2\u2014The inflammatory response. Introductory Immunology, Academic Press. 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