{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,3,25]],"date-time":"2026-03-25T06:08:41Z","timestamp":1774418921491,"version":"3.50.1"},"reference-count":57,"publisher":"MDPI AG","issue":"22","license":[{"start":{"date-parts":[[2023,11,8]],"date-time":"2023-11-08T00:00:00Z","timestamp":1699401600000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Molecules"],"abstract":"<jats:p>In this investigation, 4-antipyrinecarboxaldhyde was reacted with methyl hydrazinecarbodithioate to afford the carbodithioate derivative 3. The as-prepared carbodithioate derivative 3 is considered to be a key molecule for the preparation of new antipyrine-1,3,4-thiadiazole-based molecules (4\u20139) through its reaction with the appropriate hydrazonoyl halides. Furthermore, a typical Biginelli three-component cyclocondensation reaction involving ethyl acetoacetate, 4-antipyrinecarboxaldhyde, and thiourea under the standard conditions is carried out in the presence of sulfuric acid to afford the corresponding antipyrine\u2013pyrimidine hybrid molecule (10). The latter was submitted to react with hydrazine monohydrate to provide the corresponding hydrazide derivative (11) which, under reaction with ethyl acetoacetate in refluxing ethanol containing catalytic amount of acetic acid, afforded the corresponding derivative (12). The structure of the newly synthesized compounds was affirmed by their spectral and microanalytical data. We also screened for their antimicrobial potential (ZOI and MIC) and conducted a kinetic study. Additionally, the mechanism of biological action was assessed by a membrane leakage assay and SEM imaging technique. Moreover, the biological activities and the binding modes of these compounds were further supplemented by an in silico docking study against E. coli \u03b2-carbonic anhydrase. The amount of cellular protein released by E. coli is directly correlated to the concentration of compound 9, which was found to be 177.99 \u00b5g\/mL following treatment with 1.0 mg\/mL of compound 9. This finding supports compound 9\u2019s antibacterial properties and explains how the formation of holes in the E. coli cell membrane results in the release of proteins from the cytoplasm. The newly synthesized compounds represent acceptable antimicrobial activities with potential action against E. coli \u03b2-carbonic anhydrase. The docking studies and antimicrobial activity test proved that compound (9) declared a greater activity than the other synthesized compounds.<\/jats:p>","DOI":"10.3390\/molecules28227491","type":"journal-article","created":{"date-parts":[[2023,11,9]],"date-time":"2023-11-09T03:42:40Z","timestamp":1699501360000},"page":"7491","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":4,"title":["Antimicrobial Potency and E. coli\u00a0\u03b2-Carbonic Anhydrase Inhibition Efficacy of Phenazone-Based Molecules"],"prefix":"10.3390","volume":"28","author":[{"ORCID":"https:\/\/orcid.org\/0000-0001-7474-1678","authenticated-orcid":false,"given":"Huda R. M.","family":"Rashdan","sequence":"first","affiliation":[{"name":"Chemistry of Natural and Microbial Products Department, Pharmaceutical and Drug Industries Research Institute, National Research Centre, 33 El Buhouth St., Dokki, Giza 12622, Egypt"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Gharieb S.","family":"El-Sayyad","sequence":"additional","affiliation":[{"name":"Department of Microbiology and Immunology, Faculty of Pharmacy, Ahram Canadian University (ACU), Giza 12566, Egypt"},{"name":"Department of Microbiology and Immunology, Faculty of Pharmacy, Galala University, New Galala City, Suez 43511, Egypt"},{"name":"Drug Microbiology Laboratory, Drug Radiation Research Department, National Center for Radiation Research and Technology (NCRRT), Egyptian Atomic Energy Authority (EAEA), Cairo 11765, Egypt"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Ihsan A.","family":"Shehadi","sequence":"additional","affiliation":[{"name":"Chemistry Department, College of Sciences, University of Sharjah, Sharjah 27272, United Arab Emirates"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-4616-0224","authenticated-orcid":false,"given":"Aboubakr H.","family":"Abdelmonsef","sequence":"additional","affiliation":[{"name":"Chemistry Department, Faculty of Science, South Valley University, Qena 83523, Egypt"}],"role":[{"role":"author","vocabulary":"crossref"}]}],"member":"1968","published-online":{"date-parts":[[2023,11,8]]},"reference":[{"key":"ref_1","doi-asserted-by":"crossref","first-page":"12906","DOI":"10.1002\/slct.201902376","article-title":"Synthesis of novel antipyrine derivatives possessing remarkable antimicrobial activities","volume":"4","author":"Bayrak","year":"2019","journal-title":"ChemistrySelect"},{"key":"ref_2","doi-asserted-by":"crossref","first-page":"4566","DOI":"10.1016\/j.ejmech.2011.07.035","article-title":"Design and synthesis of some new thiophene, thienopyrimidine and thienothiadiazine derivatives of antipyrine as potential antimicrobial agents","volume":"46","author":"Aly","year":"2011","journal-title":"Eur. 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